Multicomponent reactions II

Editor: Prof. Thomas J. J. Müller
Heinrich-Heine-Universität Düsseldorf

This Thematic Series on multicomponent reactions (MCR) is a continuation of the previously released series two years ago and again presents a snap shot of this highly dynamic field. With the traditional formats of letters, full papers, and reviews it spans the broad range of modern chemistry, including organocatalytic, organometallic, transition metal-catalyzed, radical reactions, condensation and isonitrile-based MCR. Biologically active compounds and photonic properties are addressed as well as mechanistic studies and models. MCR are intriguing for industrial applications, but they are also challenging for academia, in particular for the minute and sophisticated fine-tuning of reactivity and selectivity, which is required to concatenate elementary steps to novel sequences. The interested reader – whether an expert in the field or a newcomer – will find exciting reports from the current realm of MCR chemistry.

Multicomponent reactions II

Thomas J. J. Müller

Editorial
Published 09 Jan 2014

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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 115–116, doi:10.3762/bjoc.10.7

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Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

Amit Kumar,
Dipak D. Vachhani,
Sachin G. Modha,
Sunil K. Sharma,
Virinder S. Parmar and
Erik V. Van der Eycken

Full Research Paper
Published 14 Oct 2013

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1. Graphical Abstract
2. Scheme 1: Gold-catalyzed approaches towards spiroindolines.
  
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3. Scheme 2: Plausible mechanism for the domino sequence.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2097–2102, doi:10.3762/bjoc.9.246

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Efficient synthesis of dihydropyrimidinones via a three-component Biginelli-type reaction of urea, alkylaldehyde and arylaldehyde

Haijun Qu,
Xuejian Li,
Fan Mo and
Xufeng Lin

Full Research Paper
Published 11 Dec 2013

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1. Graphical Abstract
2. Figure 1: X-ray crystal structure of 4a.
  
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3. Scheme 1: Possible mechanism.
  
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4. Figure 2: Scope of the enantioselective reaction. Reaction conditions: 5a (10 mol %, 0.02 mmol), 1 (0.2 mmol)...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2846–2851, doi:10.3762/bjoc.9.320

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Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate

Hong Gao,
Jing Sun and
Chao-Guo Yan

Full Research Paper
Published 27 Dec 2013

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1. Graphical Abstract
2. Figure 1: Molecular structure of compound 1f.
  
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3. Figure 2: Molecular structure of compound 2a.
  
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4. Figure 3: Molecular structure of compound 2h.
  
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5. Scheme 1: The proposed reaction mechanism for the four-component reaction.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2934–2939, doi:10.3762/bjoc.9.330

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Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations

Ouldouz Ghashghaei,
Consiglia Annamaria Manna,
Esther Vicente-García,
Marc Revés and
Rodolfo Lavilla

Letter
Published 06 Jan 2014

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1. Graphical Abstract
2. Scheme 1: Azetidine formation from the interaction of imines with isocyanides.
  
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3. Scheme 2: Reaction conditions.
  
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4. Figure 1: X-ray diffraction analysis of azetidine 3a.
  
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5. Scheme 3: Stepwise mechanism for the formation of azetidine 3a.
  
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6. Scheme 4: Manifold reaction mechanism.
  
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Beilstein J. Org. Chem. 2014, 10, 12–17, doi:10.3762/bjoc.10.3

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The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

Tatyana L. Pavlovskaya,
Fedor G. Yaremenko,
Victoria V. Lipson,
Svetlana V. Shishkina,
Oleg V. Shishkin,
Vladimir I. Musatov and
Alexander S. Karpenko

Full Research Paper
Published 09 Jan 2014

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1. Graphical Abstract
2. Figure 1: The NOE correlations of the signals in ¹H NMR spectra of compounds 4b–4d.
  
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3. Figure 2: Molecular structure of spirooxindole 4a according to X-ray diffraction data.
  
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4. Figure 3: The NOE correlations of the signals in ¹H NMR spectrum of compound 6c.
  
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5. Figure 4: Molecular structure of spirooxindole 6a observed in crystal phase as solvate with methanol accordin...
  
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6. Scheme 1: The mechanism of the regioselective synthesis of compounds 4 and 6.
  
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7. Figure 5: Conformations of acrylamide and benzoylacrylic acid.
  
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8. Figure 6: The Fukui function indices of acrylamide, azomethine ylide and benzoylacrylic acid.
  
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9. Scheme 2: The synthesis of compounds 7a–7c.
  
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10. Figure 7: The selected COSY, NOESY and HMBC correlations of the signals in the ¹H and ¹³C NMR spectra of comp...
  
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11. Scheme 3: Tentative reaction mechanism for the decarboxylative cyclative rearrangement of the initial three-c...
  
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Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

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Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes

Moustafa Sherief Moustafa,
Saleh Mohammed Al-Mousawi,
Maghraby Ali Selim,
Ahmed Mohamed Mosallam and
Mohamed Hilmy Elnagdi

Full Research Paper
Published 14 Jan 2014

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1. Graphical Abstract
2. Scheme 1: Reaction of active methylenenitriles with α,β-unsaturated ketones 1.
  
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3. Scheme 2: Synthesis of 2-amino-4-phenyl-3-cyanopyridines 2.
  
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4. Scheme 3: Synthesis of polysubstituted benzenes 3.
  
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5. Scheme 4: Syntheses of compound 9 and compounds 13a,b.
  
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6. Figure 1: X-ray crystal structure of 9.
  
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7. Figure 2: X-ray crystal structure of 13a.
  
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8. Figure 3: X-ray crystal structure of 18.
  
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9. Scheme 5: Syntheses of compounds 18 and 21.
  
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10. Figure 4: X-ray crystal structure of 21.
  
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11. Figure 5: X-ray crystal structure of 26.
  
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12. Scheme 6: Syntheses of compound 26.
  
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13. Figure 6: X-ray crystal structure of 27a.
  
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14. Scheme 7: Syntheses of compound 28a,b.
  
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15. Figure 7: X-ray crystal structure of 28b.
  
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16. Figure 8: X-ray crystal structure of 31a.
  
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17. Figure 9: X-ray crystal structure of 31b.
  
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18. Scheme 8: Syntheses of compound 31a,b.
  
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19. Scheme 9: Syntheses of compound 33a,b.
  
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20. Figure 10: X-ray crystal structure of 33a.
  
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21. Scheme 10: Syntheses of compound 37a–c.
  
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22. Figure 11: X-ray crystal structure of 37a.
  
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23. Figure 12: X-ray crystal structure of 37b.
  
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24. Scheme 11: Syntheses of compounds 38–40.
  
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25. Figure 13: X-ray crystal structure of 39.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 141–149, doi:10.3762/bjoc.10.11

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One-pot synthesis of cyanohydrin derivatives from alkyl bromides via incorporation of two one-carbon components by consecutive radical/ionic reactions

Shuhei Sumino,
Akira Fusano,
Hiroyuki Okai,
Takahide Fukuyama and
Ilhyong Ryu

Letter
Published 14 Jan 2014

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1. Graphical Abstract
2. Scheme 1: Sequential radical formylation and derivatization.
  
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3. Scheme 2: Examination of cyanide source.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 150–154, doi:10.3762/bjoc.10.12

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Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues

Nadezhda V. Sokolova,
Valentine G. Nenajdenko,
Vladimir B. Sokolov,
Daria V. Vinogradova,
Elena F. Shevtsova,
Ludmila G. Dubova and
Sergey O. Bachurin

Full Research Paper
Published 15 Jan 2014

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1. Graphical Abstract
2. Figure 1: Structures of dimebon and SS peptides.
  
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3. Scheme 1: Synthesis of starting N-substituted tetrahydro-γ-carbolines 3a–d.
  
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4. Scheme 2: Synthesis of peptides 5 through the Ugi reaction.
  
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5. Scheme 3: Synthesis of N-substituted tetrahydro-γ-carbolines containing protected peptide residues.
  
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6. Scheme 4: Synthesis of dihydrochloride salts 7a–g.
  
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Beilstein J. Org. Chem. 2014, 10, 155–162, doi:10.3762/bjoc.10.13

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Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

Lisa Moni,
Luca Banfi,
Andrea Basso,
Alice Brambilla and
Renata Riva

Letter
Published 17 Jan 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of benzyl azides. a) BnBr, K₂CO₃, acetone or DMF, rt or 60 °C (for 2d); b) 1) MsCl, Et₃N,...
  
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3. Scheme 2: Synthesis of dihydrobenzoxazepinones 10.
  
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Beilstein J. Org. Chem. 2014, 10, 209–212, doi:10.3762/bjoc.10.16

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Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

Ludovic Eberlin,
Fabien Tripoteau,
François Carreaux,
Andrew Whiting and
Bertrand Carboni

Review
Published 22 Jan 2014

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1. Graphical Abstract
2. Scheme 1: 1-Boron-substituted 1,3-diene in a tandem cycloaddition [4 + 2]/allylboration sequence.
  
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3. Scheme 2: Lewis acid catalyst in the tandem cycloaddition [4 + 2]/allylboration sequence.
  
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4. Scheme 3: Synthesis of an advanced precursor of clerodin.
  
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5. Scheme 4: Intramolecular Diels–Alder/allylboration sequence.
  
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6. Scheme 5: Diastereoselective Diels–Alder reaction with N-phenylmaleimide and 4-phenyltriazoline-3,5-dione.
  
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7. Scheme 6: Asymmetric synthesis of a α-hydroxyalkylcyclohexane.
  
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8. Scheme 7: Tandem [4 + 2]-cycloaddition/allylboration of 3-silyloxy- and 4-alkoxy-dienyl boronates.
  
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9. Scheme 8: Metal-mediated cycloisomerization/Diels–Alder reaction/allylboration sequence.
  
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10. Scheme 9: Cobalt-catalyzed Diels–Alder/allylboration sequence.
  
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11. Scheme 10: A two-step reaction sequence for the synthesis of tetrahydronaphthalenes 12.
  
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12. Scheme 11: Tandem sequence based on the Petasis borono–Mannich reaction as first key step.
  
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13. Scheme 12: One-pot tandem dimerization/allylboration reaction of 1,3-diene-2-boronate.
  
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14. Scheme 13: Tandem Diels–Alder/cross-coupling reactions of trifluoroborates 15.
  
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15. Scheme 14: Diels–Alder/cross-coupling reactions of 16.
  
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16. Scheme 15: Metal catalyzed tandem Diels–Alder/hydrolysis reactions.
  
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17. Scheme 16: Synthesis of anti-1,5-diols 18 by triple aldehyde addition.
  
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18. Scheme 17: Catalytic enantioselective three-component hetero-[4 + 2]-cycloaddition/allylboration sequence.
  
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19. Scheme 18: Synthesis of natural products using the catalytic enantioselective HDA/allylboration sequence.
  
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20. Scheme 19: Total synthesis of a thiomarinol derivative.
  
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21. Scheme 20: Synthesis of an advanced intermediate 27 for the east fragment of palmerolide A.
  
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22. Scheme 21: Bicyclic piperidines from tandem aza-[4 + 2]-cycloaddition/allylboration.
  
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23. Scheme 22: Hydrogenolysis reactions of hydrazinopiperidines.
  
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24. Scheme 23: Tandem aza-[4 + 2]-cycloaddition/allylboration/retrosulfinyl-ene sequence.
  
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25. Scheme 24: Boronated heterodendralene 32 in [4 + 2]-cycloadditions.
  
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26. Scheme 25: Synthesis of tricyclic imides derivatives.
  
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27. Scheme 26: Synthesis of 37 via a HDA/allylboration/DA sequence.
  
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28. Scheme 27: Diels–Alder/allylboration sequence.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

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Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

Jie-Ping Wan,
Yunfang Lin,
Kaikai Hu and
Yunyun Liu

Letter
Published 29 Jan 2014

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1. Graphical Abstract
2. Figure 1: Some DHPMs-based lead compounds.
  
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3. Scheme 1: Regioselective 1,3-thiazines and DHPMs via aldehydes, ureas/thioureas and alkynes.
  
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4. Scheme 2: Synthesis of enamino ester intermediate and its transformation to DHPM.
  
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5. Scheme 3: Proposed reaction mechanism.
  
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Beilstein J. Org. Chem. 2014, 10, 287–292, doi:10.3762/bjoc.10.25

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The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

Mrinal K. Bera,
Moisés Domínguez,
Paul Hommes and
Hans-Ulrich Reissig

Full Research Paper
Published 13 Feb 2014

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1. Graphical Abstract
2. Scheme 1: Flögel-three-component reaction of lithiated alkoxyallenes, nitriles and carboxylic acids providing...
  
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3. Scheme 2: Synthesis of bis(β-ketoenamides) 13–15 by three-component reactions of lithiated methoxyallene 8 wi...
  
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4. Scheme 3: Cyclocondensations of β-ketoenamides 13 and 14 to 4-hydroxypyridines 16, 18a and 18b, their subsequ...
  
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5. Scheme 4: Cyclocondensations of β-ketoenamides 13–15 with ammonium acetate to bis(pyrimidine) derivatives 23a...
  
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6. Scheme 5: Conversion of mono-pyrimidine derivative 24b into unsymmetrically substituted biphenylen-bridged py...
  
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7. Scheme 6: Condensation of β-ketoenamides 14 and 20 with hydroxylamine hydrochloride to pyridine-N-oxides 28 a...
  
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8. Scheme 7: Riley oxidation of bis(pyrimidine) derivative 23a and conversion of diol 32a into macrocycle 34.
  
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9. Figure 1: Optimized geometries of (a) E-configured and (b) Z-configured macrocycle 34 at B3LYP/6-31G(d,p) lev...
  
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10. Scheme 8: Dihydroxylation of the macrocyclic olefin 34 to diol 35 and subsequent esterification to the bis-(R...
  
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Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

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A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides

Antoine Pignon,
Erwan Le Gall and
Thierry Martens

Letter
Published 17 Feb 2014

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1. Graphical Abstract
2. Scheme 1: Possible reaction mechanism.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 425–431, doi:10.3762/bjoc.10.39

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A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones

Pitchaimani Prasanna,
Pethaiah Gunasekaran,
Subbu Perumal and
J. Carlos Menéndez

Full Research Paper
Published 21 Feb 2014

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1. Graphical Abstract
2. Scheme 1: Summary of the transformations involved in the synthesis of compounds 5, containing chromone and β-...
  
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3. Scheme 2: Synthesis of compounds 5.
  
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4. Figure 1: X-ray structure of compound 5h.
  
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5. Scheme 3: Initial mechanistic proposal to explain the formation of compounds 5 that was ruled out by deuterat...
  
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6. Scheme 4: Alternative mechanistic proposal based on a carbon monoxide-induced deoxygenation.
  
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Beilstein J. Org. Chem. 2014, 10, 459–465, doi:10.3762/bjoc.10.43

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Silver and gold-catalyzed multicomponent reactions

Giorgio Abbiati and
Elisabetta Rossi

Review
Published 26 Feb 2014

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1. Graphical Abstract
2. Scheme 1: General reaction mechanism for Ag(I)-catalyzed A³-coupling reactions.
  
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3. Scheme 2: A³-coupling reaction catalyzed by polystyrene-supported NHC–silver halides.
  
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4. Figure 1: Various NHC–Ag(I) complexes used as catalysts for A³-coupling.
  
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5. Scheme 3: Proposed reaction mechanism for NHC–AgCl catalyzed A³-coupling reactions.
  
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6. Scheme 4: Liu’s synthesis of pyrrole-2-carboxaldehydes 4.
  
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7. Scheme 5: Proposed reaction mechanism for Liu’s synthesis of pyrrole-2-carboxaldehydes 4.
  
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8. Scheme 6: Gold-catalyzed synthesis of propargylamines 1.
  
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9. Scheme 7: A³-coupling catalyzed by phosphinamidic Au(III) metallacycle 6.
  
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10. Scheme 8: Gold-catalyzed KA²-coupling.
  
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11. Scheme 9: A³-coupling applied to aldehyde-containing oligosaccharides 8.
  
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12. Scheme 10: A³-MCR for the preparation of propargylamine-substituted indoles 9.
  
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13. Scheme 11: A³-coupling interceded synthesis of furans 12.
  
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14. Scheme 12: A³/KA²-coupling mediated synthesis of functionalized dihydropyrazoles 13 and polycyclic dihydropyra...
  
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15. Scheme 13: Au(I)-catalyzed entry to cyclic carbamimidates 17 via an A³-coupling-type approach.
  
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16. Scheme 14: Proposed reaction mechanism for the Au(I)-catalyzed synthesis of cyclic carbamimidates 17.
  
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17. Figure 2: Chiral trans-1-diphenylphosphino-2-aminocyclohexane–Au(I) complex 20.
  
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18. Scheme 15: A³-coupling-type synthesis of oxazoles 21 catalyzed by Au(III)–salen complex.
  
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19. Scheme 16: Proposed reaction mechanism for the synthesis of oxazoles 21.
  
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20. Scheme 17: Synthesis of propargyl ethyl ethers 24 by an A³-coupling-type reaction.
  
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21. Scheme 18: General mechanism of Ag(I)-catalyzed MCRs of 2-alkynylbenzaldehydes, amines and nucleophiles.
  
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22. Scheme 19: General synthetic pathway to 1,3-disubstituted-1,2-dihydroisoquinolines.
  
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23. Scheme 20: Synthesis of 1,3-disubstituted-1,2-dihydroisoquinolines 29.
  
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24. Scheme 21: Synthesis of 1,3-disubstituted-1,2-dihydroisoquinolines 35 and 36.
  
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25. Scheme 22: Rh(II)/Ag(I) co-catalyzed synthesis of 1,3-disubstituted-1,2-dihydroisoquinolines 40.
  
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26. Scheme 23: General synthetic pathway to 2-amino-1,2-dihydroquinolines.
  
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27. Scheme 24: Synthesis of 2-amino-1,2-dihydroquinolines 47.
  
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28. Scheme 25: Synthesis of tricyclic H-pyrazolo[5,1-a]isoquinoline 48.
  
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29. Scheme 26: Synthesis of tricyclic H-pyrazolo[5,1-a]isoquinolines 48.
  
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30. Scheme 27: Cu(II)/Ag(I) catalyzed synthesis of H-pyrazolo[5,1-a]isoquinolines 48.
  
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31. Scheme 28: Synthesis of 2-aminopyrazolo[5,1-a]isoquinolines 53.
  
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32. Scheme 29: Synthesis of 1-(isoquinolin-1-yl)guanidines 55.
  
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33. Scheme 30: Ag(I)/Cu(I) catalyzed synthesis of 2-amino-H-pyrazolo[5,1-a]isoquinolines 58.
  
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34. Scheme 31: Ag(I)/Ni(II) co-catalyzed synthesis of 3,4-dihydro-1H-pyridazino[6,1-a]isoquinoline-1,1-dicarboxyla...
  
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35. Scheme 32: Ag(I) promoted activation of the α-carbon atom of the isocyanide group.
  
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36. Scheme 33: Synthesis of dihydroimidazoles 65.
  
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37. Scheme 34: Synthesis of oxazoles 68.
  
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38. Scheme 35: Stereoselective synthesis of chiral butenolides 71.
  
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39. Scheme 36: Proposed reaction mechanism for the synthesis of butenolides 71.
  
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40. Scheme 37: Stereoselective three-component approach to pirrolidines 77 by means of a chiral auxiliary.
  
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41. Scheme 38: Stereoselective three-component approach to pyrrolidines 81 and 82 by means of a chiral catalyst.
  
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42. Scheme 39: Synthesis of substituted five-membered carbocyles 86.
  
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43. Scheme 40: Synthesis of regioisomeric arylnaphthalene lactones.
  
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44. Scheme 41: Enantioselective synthesis of spiroacetals 96 by Fañanás and Rodríguez [105].
  
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45. Scheme 42: Enantioselective synthesis of spiroacetals 101 by Gong [106].
  
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46. Scheme 43: Synthesis of polyfunctionalized fused bicyclic ketals 103 and bridged tricyclic ketals 104.
  
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47. Scheme 44: Proposed reaction mechanism for the synthesis of ketals 103 and 104.
  
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48. Scheme 45: Synthesis of β-alkoxyketones 108.
  
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49. Scheme 46: Synthesis of N-methyl-1,4-dihydropyridines 112.
  
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50. Scheme 47: Synthesis of tetrahydrocarbazoles 115–117.
  
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51. Scheme 48: Plausible reaction mechanism for the synthesis of tetrahydrocarbazoles 115–117.
  
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52. Scheme 49: Carboamination, carboalkoxylation and carbolactonization of terminal alkenes.
  
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53. Scheme 50: Oxyarylation of alkenes with arylboronic acids and Selectfluor as reoxidant.
  
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54. Scheme 51: Proposed reaction mechanism for oxyarylation of alkenes.
  
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55. Scheme 52: Oxyarylation of alkenes with arylsilanes and Selectfluor as reoxidant.
  
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56. Scheme 53: Oxyarylation of alkenes with arylsilanes and IBA as reoxidant.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

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Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates

Xiaoyu Yan,
Chao Chen and
Chanjuan Xi

Full Research Paper
Published 28 Feb 2014

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1. Graphical Abstract
2. Scheme 1: Transformation of alkynes to olefins.
  
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3. Scheme 2: Carbozirconation of alkynes via zirconacyclopentenes.
  
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4. Scheme 3: TCQ-promoted reductive elimination of arylzirconate.
  
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5. Scheme 4: TCQ-promoted arylzirconation of diphenylacetylene.
  
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6. Scheme 5: Oxidative dimerization of 4a.
  
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7. Scheme 6: Possible reaction mechanism.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 528–534, doi:10.3762/bjoc.10.48

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Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

Gijs Koopmanschap,
Eelco Ruijter and
Romano V.A. Orru

Review
Published 04 Mar 2014

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1. Graphical Abstract
2. Scheme 1: The proposed mechanism of the Passerini reaction.
  
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3. Scheme 2: The PADAM-strategy to α-hydroxy-β-amino amide derivatives 7. An additional oxidation provides α-ket...
  
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4. Scheme 3: The general accepted Ugi-mechanism.
  
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5. Scheme 4: Three commonly applied Ugi/cyclization approaches. a) UDC-process, b) UAC-sequence, c) UDAC-combina...
  
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6. Scheme 5: Ugi reaction that involves the condensation of Armstrong’s convertible isocyanide.
  
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7. Scheme 6: Mechanism of the U-4C-3CR towards bicyclic β-lactams.
  
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8. Scheme 7: The Ugi 4C-3CR towards oxabicyclo β-lactams.
  
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9. Scheme 8: Ugi MCR between an enantiopure monoterpene based β-amino acid, aldehyde and isocyanide resulting in...
  
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10. Scheme 9: General MCR for β-lactams in water.
  
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11. Scheme 10: a) Ugi reaction for β-lactam-linked peptidomimetics. b) Varying the β-amino acid resulted in β-lact...
  
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12. Scheme 11: Ugi-4CR followed by a Pd-catalyzed S_n2 cyclization.
  
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13. Scheme 12: Ugi-3CR of dipeptide mimics from 2-substituted pyrrolines.
  
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14. Scheme 13: Joullié–Ugi reaction towards 2,5-disubstituted pyrrolidines.
  
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15. Scheme 14: Further elaboration of the Ugi-scaffold towards bicyclic systems.
  
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16. Scheme 15: Dihydroxyproline derivatives from an Ugi reaction.
  
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17. Scheme 16: Diastereoselective Ugi reaction described by Banfi and co-workers.
  
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18. Scheme 17: Similar Ugi reaction as in Scheme 16 but with different acids and two chiral isocyanides.
  
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19. Scheme 18: Highly diastereoselective synthesis of pyrrolidine-dipeptoids via a MAO-N/MCR-procedure.
  
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20. Scheme 19: MAO-N/MCR-approach towards the hepatitis C drug telaprevir.
  
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21. Scheme 20: Enantioselective MAO-U-3CR procedure starting from chiral pyrroline 64.
  
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22. Scheme 21: Synthesis of γ-lactams via an UDC-sequence.
  
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23. Scheme 22: Utilizing bifunctional groups to provide bicyclic γ-lactam-ketopiperazines.
  
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24. Scheme 23: The Ugi reaction provided both γ- as δ-lactams depending on which inputs were used.
  
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25. Scheme 24: The sequential Ugi/RCM with olefinic substrates provided bicyclic lactams.
  
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26. Scheme 25: a) The structural and dipole similarities of the triazole unit with the amide bond. b) The copper-c...
  
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27. Scheme 26: The Ugi/Click sequence provided triazole based peptidomimetics.
  
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28. Scheme 27: The Ugi/Click reaction as described by Nanajdenko.
  
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29. Scheme 28: The Ugi/Click-approach by Pramitha and Bahulayan.
  
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30. Scheme 29: The Ugi/Click-combination by Niu et al.
  
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31. Scheme 30: Triazole linked peptidomimetics obtained from two separate MCRs and a sequential Click reaction.
  
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32. Scheme 31: Copper-free synthesis of triazoles via two MCRs in one-pot.
  
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33. Scheme 32: The sequential Ugi/Paal–Knorr reaction to afford pyrazoles.
  
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34. Scheme 33: An intramolecular Paal–Knorr condensation provided under basic conditions pyrazolones.
  
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35. Scheme 34: Similar cyclization performed under acidic conditions provided pyrazolones without the trifluoroace...
  
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36. Scheme 35: The Ugi-4CR towards 2,4-disubstituted thiazoles.
  
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37. Scheme 36: Solid phase approach towards thiazoles.
  
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38. Scheme 37: Reaction mechanism of formation of thiazole peptidomimetics containing an additional β-lactam moiet...
  
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39. Scheme 38: The synthesis of the trisubstituted thiazoles could be either performed via an Ugi reaction with pr...
  
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40. Scheme 39: Performing the Ugi reaction with DMB-protected isocyanide gave access to either oxazoles or thiazol...
  
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41. Scheme 40: Ugi/cyclization-approach towards 2,5-disubstituted thiazoles. The Ugi reaction was performed with d...
  
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42. Scheme 41: Further derivatization of the thiazole scaffold.
  
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43. Scheme 42: Three-step procedure towards the natural product bacillamide C.
  
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44. Scheme 43: Ugi-4CR to oxazoles reported by Zhu and co-workers.
  
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45. Scheme 44: Ugi-based synthesis of oxazole-containing peptidomimetics.
  
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46. Scheme 45: TMNS₃ based Ugi reaction for peptidomimics containing a tetrazole.
  
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47. Scheme 46: Catalytic cycle of the enantioselective Passerini reaction towards tetrazole-based peptidomimetics.
  
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48. Scheme 47: Tetrazole-based peptidomimetics via an Ugi reaction and a subsequent sigmatropic rearrangement.
  
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49. Scheme 48: Resin-bound Ugi-approach towards tetrazole-based peptidomimetics.
  
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50. Scheme 49: Ugi/cyclization approach towards γ/δ/ε-lactam tetrazoles.
  
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51. Scheme 50: Ugi-3CR to pipecolic acid-based peptidomimetics.
  
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52. Scheme 51: Staudinger–Aza-Wittig/Ugi-approach towards pipecolic acid peptidomimetics.
  
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53. Figure 1: The three structural isomers of diketopiperazines. The 2,5-DKP isomer is most common.
  
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54. Scheme 52: UDC-approach to obtain 2,5-DKPs, either using Armstrong’s isocyanide or via ethylglyoxalate.
  
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55. Scheme 53: a) Ugi reaction in water gave either 2,5-DKP structures or spiro compounds. b) The Ugi reaction in ...
  
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56. Scheme 54: Solid-phase approach towards diketopiperazines.
  
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57. Scheme 55: UDAC-approach towards DKPs.
  
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58. Scheme 56: The intermediate amide is activated as leaving group by acid and microwave assisted organic synthes...
  
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59. Scheme 57: UDC-procedure towards active oxytocin inhibitors.
  
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60. Scheme 58: An improved stereoselective MCR-approach towards the oxytocin inhibitor.
  
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61. Scheme 59: The less common Ugi reaction towards DKPs, involving a S_n2-substitution.
  
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62. Figure 2: Spatial similarities between a natural β-turn conformation and a DKP based β-turn mimetic [158].
  
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63. Scheme 60: Ugi-based syntheses of bicyclic DKPs. The amine component is derived from a coupling between (R)-N-...
  
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64. Scheme 61: Ugi-based synthesis of β-turn and γ-turn mimetics.
  
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65. Figure 3: Isocyanide substituted 3,4-dihydropyridin-2-ones, dihydropyridines and the Freidinger lactams. Bio-...
  
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66. Scheme 62: The mechanism of the 4-CR towards 3,4-dihydropyridine-2-ones 212.
  
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67. Scheme 63: a) Multiple MCR-approach to provide DHP-peptidomimetic in two-steps. b) A one-pot 6-CR providing th...
  
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68. Scheme 64: The MCR–alkylation–MCR procedure to obtain either tetrapeptoids or depsipeptides.
  
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69. Scheme 65: U-3CR/cyclization employing semicarbazone as imine component gave triazine based peptidomimetics.
  
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70. Scheme 66: 4CR towards triazinane-diones.
  
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71. Scheme 67: The MCR–alkylation–IMCR-sequence described by our group towards triazinane dione-based peptidomimet...
  
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72. Scheme 68: Ugi-4CR approaches followed by a cyclization to thiomorpholin-ones (a) and pyrrolidines (b).
  
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73. Scheme 69: UDC-approach for benzodiazepinones.
  
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74. Scheme 70: Ugi/Mitsunobu sequence to BDPs.
  
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75. Scheme 71: A UDAC-approach to BDPs with convertible isocyanides. The corresponding amide is cleaved by microwa...
  
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76. Scheme 72: microwave assisted post condensation Ugi reaction.
  
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77. Scheme 73: Benzodiazepinones synthesized via the post-condensation Ugi/ Staudinger–Aza-Wittig cyclization.
  
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78. Scheme 74: Two Ugi/cyclization approaches utilizing chiral carboxylic acids. Reaction (a) provided the product...
  
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79. Scheme 75: The mechanism of the Gewald-3CR includes three base-catalysed steps involving first a Knoevnagel–Co...
  
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80. Scheme 76: Two structural 1,4-thienodiazepine-2,5-dione isomers by U-4CR/cyclization.
  
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81. Scheme 77: Tetrazole-based diazepinones by UDC-procedure.
  
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82. Scheme 78: Tetrazole-based BDPs via a sequential Ugi/hydrolysis/coupling.
  
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83. Scheme 79: MCR synthesis of three different tricyclic BPDs.
  
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84. Scheme 80: Two similar approaches both involving an Ugi reaction and a Mitsunobu cyclization.
  
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85. Scheme 81: Mitsunobu–Ugi-approach towards dihydro-1,4-benzoxazepines.
  
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86. Scheme 82: Ugi reaction towards hetero-aryl fused 5-oxo-1,4-oxazepines.
  
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87. Scheme 83: a) Ugi/RCM-approach towards nine-membered peptidomimetics b) Sequential peptide-coupling, deprotect...
  
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88. Scheme 84: Ugi-based synthesis towards cyclic RGD-pentapeptides.
  
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89. Scheme 85: Ugi/MCR-approach towards 12–15 membered macrocycles.
  
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90. Scheme 86: Stereoselective Ugi/RCM approach towards 16-membered macrocycles.
  
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91. Scheme 87: Passerini/RCM-sequence to 22-membered macrocycles.
  
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92. Scheme 88: UDAC-approach towards 12–18-membered depsipeptides.
  
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93. Figure 4: Enopeptin A with its more active derivative ADEP-4.
  
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94. Scheme 89: a) The Joullié–Ugi-approach towards ADEP-4 derivatives b) Ugi-approach for the α,α-dimethylated der...
  
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95. Scheme 90: Ugi–Click-strategy for 15-membered macrocyclic glyco-peptidomimetics.
  
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96. Scheme 91: Ugi/Click combinations provided macrocycles containing both a triazole and an oxazole moiety.
  
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97. Scheme 92: a) A solution-phase procedure towards macrocycles. b) Alternative solid-phase synthesis as was repo...
  
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98. Scheme 93: Ugi/cyclization towards cyclophane based macrocycles.
  
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99. Scheme 94: PADAM-strategy towards eurystatin A.
  
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100. Scheme 95: PADAM-approach for cyclotheanamide.
  
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101. Scheme 96: A triple MCR-approach affording RGD-pentapeptoids.
  
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102. Scheme 97: Ugi-MiBs-approach towards peptoid macrocycles.
  
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103. Scheme 98: Passerini-based MiB approaches towards macrocycles 345 and 346.
  
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104. Scheme 99: Macrocyclic peptide formation by the use of amphoteric aziridine-based aldehydes.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Full Text

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

Christian Muschelknautz,
Robin Visse,
Jan Nordmann and
Thomas J. J. Müller

Full Research Paper
Published 05 Mar 2014

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1. Graphical Abstract
2. Figure 1: Linear push–pull solid-state diene lumophores with conformationally flexible and fixed acceptor moi...
  
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3. Scheme 1: Three-component synthesis of 1-styryleth-2-enylideneindolones 8.
  
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4. Figure 2: DFT-computed energy differences of the stereoisomers of 2Z,4Z-8a and 2Z,4E-8a.
  
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5. Scheme 2: Three-component synthesis of 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones 10.
  
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6. Figure 3: DFT-computed energy differences of the stereoisomers of 10a and 10h.
  
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7. Scheme 3: Mechanistic rationale of the three-component sequence furnishing the 1-styryleth-2-enylideneindolon...
  
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8. Figure 4: DFT-computed (B3LYP functional, 6-31G* basis set) HOMO (left) and LUMO (right) of merocyanine 8a.
  
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9. Figure 5: Absorption and emission spectrum of the dropcasted film of compound 8a (recorded at room temperatur...
  
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10. Figure 6: Absorption spectrum of the dropcasted film of compound 10d (recorded at room temperature, normalize...
  
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11. Figure 7: Absorption spectra of compound 10h in dichloromethane (right trace) and of the dropcasted film (lef...
  
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12. Figure 8: DFT-computed (B3LYP functional, 6-311G(d,p) basis set) FMOs (HOMO, bottom; LUMO (center), and LUMO+...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51

Full Text

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

Fabian Klukas,
Alexander Grunwald,
Franziska Menschel and
Thomas J. J. Müller

Full Research Paper
Published 18 Mar 2014

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1. Graphical Abstract
2. Scheme 1: Sonogashira–Glaser sequence in DMSO as a solvent.
  
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3. Scheme 2: Pseudo five-component Sonogashira–Glaser cyclisation synthesis of 2,5-di(hetero)arylfurans 2 (^aobta...
  
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4. Figure 1: Compounds 2d (solid and THF solution) and 2n (solid and THF solution) (from left to right) under da...
  
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5. Figure 2: Selected computed minimum conformations of the 2,5-diarylfurans 2i, 2j, and 2n.
  
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6. Figure 3: Kohn–Sham HOMOs (bottom) and LUMOs (top) of the compounds 2i, 2j, and 2n (calculated on the DFT lev...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

Full Text

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

Sarah Bay,
Gamall Makhloufi,
Christoph Janiak and
Thomas J. J. Müller

Full Research Paper
Published 05 May 2014

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1. Graphical Abstract
2. Figure 1: Phenothiazine–anthraquinone dyad 1, donor-only (2) and acceptor-only (3) models assembled by Ugi 4C...
  
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3. Scheme 1: Ugi 4CR synthesis of donor–anthraquinone dyads 8.
  
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4. Scheme 2: Ugi 4CR synthesis of donor-only reference systems 10.
  
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5. Figure 2: Molecular structure of S(O)-1 (left) (30% ellipsoids, except for the CH₃CH₂ end of the hexyl group,...
  
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6. Figure 3: Cyclic voltammogram of dyad 8c (recorded in CH₂Cl₂, T = 298 K, c (8c) = 0.1 mol·L⁻¹, Pt working ele...
  
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7. Figure 4: DFT-computed (B3LYP, 6-311G*) frontier molecular orbitals HOMO (bottom) and LUMO (top) of the pheno...
  
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8. Figure 5: Normalized absorption spectra of the phenothiazine–anthraquinone dyad 8c (recorded in CH₂Cl₂, c (8c...
  
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9. Figure 6: Absorption spectra of Do–anthraquinone dyads 8c (top) and 8e (bottom) with the corresponding refere...
  
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10. Figure 7: Normalized absorption and emission spectra of Ugi-donor compounds 2 and 10 (recorded in CH₂Cl₂, T =...
  
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11. Figure 8: Emission spectra of donor-only system 2 phenothiazine–anthraquinone dyads 8a,b (top), and the donor...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

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Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

Angélica de Fátima S. Barreto,
Otilie E. Vercillo,
Ludger A. Wessjohann and
Carlos Kleber Z. Andrade

Letter
Published 05 May 2014

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1. Graphical Abstract
2. Figure 1: Sansalvamide A (1) and its depsipeptoid analogues (2).
  
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3. Figure 2: Generic structures of (a) peptide, (b) peptoid, (c) depsipeptide and (d) depsipeptoid.
  
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4. Figure 3: Structures of six pentadepsipeptoid analogues of San A.
  
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5. Scheme 1: Retrosynthetic analysis of the cyclic depsipeptoids.
  
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6. Scheme 2: Synthesis of acyclic depsipeptoids 11a,b.
  
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7. Scheme 3: Synthesis of macrocycles 2a-f.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1017–1022, doi:10.3762/bjoc.10.101

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Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles

Yogesh Kumar,
Vijay Bahadur,
Anil K. Singh,
Virinder S. Parmar,
Erik V. Van der Eycken and
Brajendra K. Singh

Full Research Paper
Published 24 Jun 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles.
  
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3. Scheme 2: Plausible mechanism for the synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-b...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1413–1420, doi:10.3762/bjoc.10.145

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Multicomponent reactions in nucleoside chemistry

Mariola Koszytkowska-Stawińska and
Włodzimierz Buchowicz

Review
Published 29 Jul 2014

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1. Graphical Abstract
2. Figure 1: Selected chemical modifications of natural ribose or 2'-deoxyribose nucleosides leading to the deve...
  
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3. Scheme 1: (a) Classical Mannich reaction; (b) general structures of selected hydrogen active components and s...
  
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4. Scheme 2: Reagents and reaction conditions: i. H₂O or H₂O/EtOH, 60–100 °C, 7 h–10 d; ii. H₂, Pd/C or PtO₂; ii...
  
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5. Scheme 3: Reagents and reaction conditions: i. H₂O, 90 °C, overnight.
  
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6. Scheme 4: Reagents and reaction conditions: i. AcOH, H₂O, 60 °C, 12 h-5 d; ii. AcOH, H₂O, 60 °C, 8 h.
  
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7. Scheme 5: Reagents and reaction conditions: i. CuBr, THF, reflux, 0.5 h; ii. n-Bu₄NF·3H₂O, THF, rt, 2 h.
  
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8. Scheme 6: Reagents and reaction conditions: i. [bmim][PF₆], 80 °C, 5–8 h.
  
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9. Scheme 7: Reagents and reaction conditions: i. EtOH, reflux, 24 h.
  
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10. Scheme 8: Reagents and reaction conditions: i. NaOAc, H₂O, 95 °C, 1–16 h; ii. NaOAc, H₂O, 95 °C, 1 h.
  
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11. Scheme 9: Reagents and reaction conditions: i. a. 37% aq HCl, MeOH; b. NaOAc, 1,4-dioxane, H₂O, 100 °C, overn...
  
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12. Scheme 10: Reagents and reaction conditions: i. DMAP, DCC, MeOH, rt, 1 h.
  
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13. Scheme 11: The Kabachnik–Fields reaction.
  
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14. Scheme 12: Reagents and reaction conditions: i. 60 °C, 3 h; ii. 80 °C, 2 h.
  
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15. Scheme 13: The four-component Ugi reaction.
  
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16. Scheme 14: Reagents and reaction conditions: i. MeOH, rt, 2–3 d, yields not given.
  
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17. Scheme 15: Reagents and reaction conditions: i. MeOH/CH₂Cl₂ (1:1), rt, 24 h, yield not given; ii. 6 N aq HCl, ...
  
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18. Scheme 16: Reagents and reaction conditions: i. MeOH/H₂O, rt, 26 h; ii. aq AcOH, reflux, 50%; iii. reversed ph...
  
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19. Scheme 17: Reagents and reaction conditions: i. MeOH, rt, 24 h; ii. HCl, MeOH, 0 °C to rt, 6 h, then H₂O, rt, ...
  
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20. Scheme 18: Reagents and reaction conditions: i. DMF/Py/MeOH (1:1:1), rt, 48 h; ii. 10% HCl/MeOH, rt, 30 min.
  
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21. Scheme 19: Reagents and reaction conditions (R = CH₃ or H): i. CH₂Cl₂/MeOH (2:1), 35–40 °C, 2 d; ii. HF/pyridi...
  
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22. Scheme 20: Reagents and reaction conditions: i. MeOH, 76%; ii. 80% aq TFA, 100%.
  
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23. Scheme 21: Reagents and reaction conditions: i. EtOH, rt, 72 h; ii. Zn, aq NaH₂PO₄, THF, rt, 1 week; then 80% ...
  
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24. Scheme 22: Reagents and reaction conditions: i. EtOH, rt, 48 h, then silica gel chromatography, 33% for 57 (30...
  
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25. Scheme 23: Reagents and reaction conditions: i. [bmim]BF₄, 80 °C, 4 h; ii. [bmim]BF₄, 80 °C, 3 h; iii. [bmim]BF...
  
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26. Scheme 24: Reagents and reaction conditions: i. [bmim]BF₄, 80 °C.
  
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27. Scheme 25: Reagents and reaction conditions: i. H₃PW₁₂O₄₀ (2 mol %), EtOH, 50 °C, 2–15 h; ii. H₃PW₁₂O₄₀ (2 mol...
  
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28. Scheme 26: General scheme of the Biginelli reaction.
  
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29. Scheme 27: Reagents and reaction conditions: i. EtOH, reflux.
  
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30. Scheme 28: Reagents and reaction conditions: i. Bu₄N⁺HSO₄⁻, diethylene glycol, 120 °C, 1.5–3 h.
  
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31. Scheme 29: Reagents and reaction conditions: i. BF₃·Et₂O, CuCl, AcOH, THF, 65 °C, 24 h; ii. Yb(OTf)₃, THF, ref...
  
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32. Scheme 30: Reagents and reaction conditions: TCT (10 mol %), rt: i. 100 min; ii. 150 min; iii. 140 min.
  
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33. Scheme 31: Reagents and reaction conditions: i. EtOH, microwave irradiation (300 W), 10 min; ii. EtOH, 75 °C, ...
  
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34. Scheme 32: The Hantzsch reaction.
  
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35. Scheme 33: Reagents and reaction conditions: TCT (10 mol %), rt, 80–150 min.
  
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36. Scheme 34: Reagents and reaction conditions: i. Yb(OTf)₃, THF, 90 °C, 12 h; ii. 4 Å molecular sieves, EtOH, 90...
  
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37. Scheme 35: Reagents and reaction conditions: i. MeOH, 50 °C, 48 h.
  
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38. Scheme 36: Reagents and reaction conditions: i. MeOH, 25 °C, 5 d.
  
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39. Scheme 37: Bu₄N⁺HSO₄⁻, diethylene glycol, 80 °C, 1–2 h.
  
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40. Scheme 38: The three-component carbopalladation of dienes on the example of buta-1,3-diene.
  
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41. Scheme 39: Reagents and reaction conditions: i. 5 mol % Pd(dba)₂, Bu₄NCl, ZnCl₂, acetonitrile or DMSO, 80 °C o...
  
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42. Scheme 40: Reagents and reaction conditions: i. 2.5 mol % Pd₂(dba)₃, tris(2-furyl)phosphine, K₂CO₃, MeCN or DM...
  
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43. Scheme 41: Reagents and reaction conditions: i. 2.5 mol % Pd₂(dba)₃, tris(2-furyl)phosphine, K₂CO₃, MeCN or DM...
  
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44. Scheme 42: The three-component Bucherer–Bergs reaction.
  
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45. Scheme 43: Reagents and reaction conditions: i. MeOH, H₂O, 70 °C, 4.5 h; ii. (1) H₂, 5% Pd/C, MeOH, 55 °C, 5 h...
  
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46. Scheme 44: Reagents and reaction conditions: i. pyridine, MgSO₄, 100 °C, 28 h, N₂; ii. DMF, 70–90 °C, 22–30 h,...
  
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47. Scheme 45: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (600 W), 6–10...
  
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48. Scheme 46: Reagents and reaction conditions: i. Montmorillonite K-10 clay, microwave irradiation (560 W), 6–10...
  
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49. Scheme 47: Reagents and reaction conditions: i. CeCl₃·7H₂O (20 mol %), NaI (20 mol %), microwave irradiation (...
  
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50. Scheme 48: Reagents and reaction conditions: i. PhI(OAc)₂ (3 mol %), microwave irradiation (45 °C), 6–9 min.
  
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51. Scheme 49: Reagents and reaction conditions: i. 117, ethyl pyruvate, TiCl₄, dichloromethane, −78 °C, 1 h; then ...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

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Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach

Barbara Palka,
Angela Di Capua,
Maurizio Anzini,
Gyté Vilkauskaité,
Algirdas Šačkus and
Wolfgang Holzer

Full Research Paper
Published 31 Jul 2014

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1. Graphical Abstract
2. Figure 1: Important drug molecules containing a trifluoromethylpyridine, respectively a trifluoromethylpyrazo...
  
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3. Scheme 1: Synthesis of the title compounds.
  
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4. Figure 2: ¹H (in italics, red), ¹³C (black), ¹⁵N (in blue) and ¹⁹F NMR (green) chemical shifts of compounds 4c...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1759–1764, doi:10.3762/bjoc.10.183

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Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

András Demjén,
Márió Gyuris,
János Wölfling,
László G. Puskás and
Iván Kanizsai

Full Research Paper
Published 08 Oct 2014

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1. Graphical Abstract
2. Scheme 1: The conventional GBB-3CR.
  
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3. Scheme 2: Plausible products 6A–H.
  
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4. Scheme 3: Synthesis of 6 via the sequential one-pot method.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 2338–2344, doi:10.3762/bjoc.10.243

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New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones

Emilian Georgescu,
Alina Nicolescu,
Florentina Georgescu,
Florina Teodorescu,
Daniela Marinescu,
Ana-Maria Macsim and
Calin Deleanu

Full Research Paper
Published 14 Oct 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of pyrrolo[1,2-a]quinoxalin-4-ones 4 and pyrrolo[1,2-a]benzimidazoles 5.
  
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3. Scheme 2: Reaction pathway leading to the formation of pyrrolo[1,2-a]quinoxalin-4-ones 4 and pyrrolo[1,2-a]be...
  
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4. Scheme 3: Novel synthetic pathway towards pyrrolo[1,2-a]quinoxalin-4-ones 10.
  
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5. Figure 1: Undecoulpled H,C-HSQC spectrum for compound 5h.
  
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6. Figure 2: Individual ¹H signal assignments based on ¹³C traces from H,C-undecoulpled-HSQC spectrum around the...
  
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7. Figure 3: NOE response as cross peaks between carbethoxy group protons and protons from positions 2 and 8 of ...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 2377–2387, doi:10.3762/bjoc.10.248

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One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines]

Chao Wang,
Yan-Hong Jiang and
Chao-Guo Yan

Full Research Paper
Published 14 Nov 2014

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1. Graphical Abstract
2. Figure 1: Molecular structure of spiro[indoline-3,4'-pyridine] 1k.
  
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3. Scheme 1: The dynamic equilibrium of cis/trans-conformation of spiro[indoline-3,4'-pyridine].
  
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4. Scheme 2: Proposed reaction mechanism for the four-component reaction.
  
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Beilstein J. Org. Chem. 2014, 10, 2671–2676, doi:10.3762/bjoc.10.281

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The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

Volodymyr V. Tkachenko,
Elena A. Muravyova,
Sergey M. Desenko,
Oleg V. Shishkin,
Svetlana V. Shishkina,
Dmytro O. Sysoiev,
Thomas J. J. Müller and
Valentin A. Chebanov

Full Research Paper
Published 17 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Some three-component reactions involving N-aryl-3-oxobutanamides.
  
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3. Scheme 2: Some Biginelli-type three-component condensations with salicylaldehyde.
  
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4. Scheme 3: Three-component heterocyclization of 5-amino-3-methylisoxazole (1), salicylaldehyde (2) and N-(2-me...
  
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5. Figure 1: The possible structure of an intermediate complex in reactions forming the heterocycles 6.
  
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6. Scheme 4: Possible pathways for the three-component reaction of 5-amino-3-methylisoxazole (1), salicylaldehyd...
  
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7. Figure 2: Alternative structures 5a and 5'a for dihydroisoxazolopyridine 5a and selected NOESY correlations.
  
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8. Figure 3: Alternative structures 6a, 6'a and 6''a for compound 6a.
  
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9. Figure 4: Selected data from NOESY experiments and relative stereochemistry of stereogenic centers at positio...
  
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10. Figure 5: Molecular structure of compound 6a according to X-ray diffraction data.
  
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Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

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Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

Martin C. N. Brauer,
Ricardo A. W. Neves Filho,
Bernhard Westermann,
Ramona Heinke and
Ludger A. Wessjohann

Full Research Paper
Published 07 Jan 2015

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1. Graphical Abstract
2. Figure 1: Apoptosis inducer C₂-symmetric 1,3-diyne-linked peptide 1 and its inactive monomer 2.
  
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3. Scheme 1: Combinatorial Glaser coupling involving acetylenes 7f, 7j and 7h.
  
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4. Figure 2: Expanded region of the ESI-MS spectrum (positive mode) and the HPLC chromatogram of the crude mixed...
  
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5. Figure 3: Growth inhibition of Bacillus subtilis by compounds 8a–j at 1 µM (15 h), and standard erythromycin ...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2015, 11, 25–30, doi:10.3762/bjoc.11.4

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