Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

Gerardo M. Ojeda,
Prabhat Ranjan,
Pavel Fedoseev,
Lisandra Amable,
Upendra K. Sharma,
Daniel G. Rivera and
Erik V. Van der Eycken

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Published 16 Oct 2019

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1. Graphical Abstract
2. Figure 1: Bioactive molecules containing a tetrazole, pyridone or isoquinolone ring.
  
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3. Scheme 1: Approaches for the synthesis of tetrazoles and isoquinolones and their interplay as designed in thi...
  
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4. Scheme 2: Scope of the Ugi-azide-4CR/deprotection/acylation sequence. Ugi-azide-4CR conducted at the 2.0 mmol...
  
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5. Scheme 3: Influence of substituents R and R² on the reaction outcome. For compounds 4k–m the overall yield in...
  
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6. Scheme 4: Influence of the alkyne and R¹ substituent on the reaction outcome.
  
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7. Scheme 5: Scope of acrylic, heterocyclic and ring-fused N-acylaminomethyl tetrazole substrates.
  
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8. Scheme 6: Proposed reaction mechanism using substrates 1a and 3a.
  
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Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

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Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

Maryna V. Murlykina,
Oleksandr V. Kolomiets,
Maryna M. Kornet,
Yana I. Sakhno,
Sergey M. Desenko,
Victoriya V. Dyakonenko,
Svetlana V. Shishkina,
Oleksandr A. Brazhko,
Vladimir I. Musatov,
Alexander V. Tsygankov,
Erik V. Van der Eycken and
Valentyn A. Chebanov

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Published 12 Jun 2019

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1. Graphical Abstract
2. Scheme 1: An overview of heterocyclic acids used in the Ugi reaction.
  
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3. Scheme 2: Synthesis of pyrazolopyridine carboxylic acids 4 [45] and 7 [45] in Doebner-type reaction.
  
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4. Figure 1: Molecular structure of N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-6-(4-methoxyphenyl)-3-...
  
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Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

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Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

Victoria V. Lipson,
Tetiana L. Pavlovska,
Nataliya V. Svetlichnaya,
Anna A. Poryvai,
Nikolay Yu. Gorobets,
Erik V. Van der Eycken,
Irina S. Konovalova,
Svetlana V. Shiskina,
Alexander V. Borisov,
Vladimir I. Musatov and
Alexander V. Mazepa

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Published 06 May 2019

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1. Graphical Abstract
2. Figure 1: 2-Aminoimidazole alkaloids from marine sponges.
  
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3. Figure 2: The Knoevenagel–Michael adduct [24] and expected products.
  
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4. Scheme 1: The three component condensation of imidazo[1,2-a]pyridine, aldehydes and Meldrum’s acid described ...
  
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5. Figure 3: Molecular structure of 1-([1,1'-biphenyl]-4-yl)-5-oxo-7-phenyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazo...
  
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6. Scheme 2: Two forms of cation 9i.
  
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7. Figure 4: Molecular structure of 3-(2-amino-4-phenyl-1H-imidazol-5-yl)-3-(p-tolyl)propanoic acid 11b accordin...
  
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8. Scheme 3: Three forms of the compound 11b in the crystal phase.
  
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9. Scheme 4: Synthesis of the mixture of compounds 13 and 14.
  
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10. Figure 5: Molecular structure of aminoimidazo[1,2-c]pyrrole 16a according to X-ray diffraction data. Thermal ...
  
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11. Scheme 5: Resonance structures of 16a.
  
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12. Figure 6: 3,3’-Spirooxindole alkaloids.
  
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13. Figure 7: Molecular structure of aminoimidazo[1,2-c]pyrrole 19a according to X-ray diffraction data. Thermal ...
  
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14. Scheme 6: Resonance structures of 19a.
  
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Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

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Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp²)–H activation and C(sp³)–H amination

Liangliang Song,
Guilong Tian,
Johan Van der Eycken and
Erik V. Van der Eycken

Letter
Published 27 Feb 2019

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1. Graphical Abstract
2. Figure 1: Selected examples of natural products with a tricyclic indolizinone scaffold.
  
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3. Scheme 1: Previous work and this approach.
  
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4. Scheme 2: Reaction scope. Reaction conditions: 1 (0.3 mmol), [RhCp*Cl₂]₂ (0.015 mmol), CsOAc (0.6 mmol), 1,4-...
  
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5. Scheme 3: Control experiments.
  
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6. Scheme 4: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2019, 15, 571–576, doi:10.3762/bjoc.15.52

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Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

Xiaochen Du,
Jianjun Huang,
Anton A. Nechaev,
Ruwei Yao,
Jing Gong,
Erik V. Van der Eycken,
Olga P. Pereshivko and
Vsevolod A. Peshkov

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Published 04 Oct 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of 2-quinolones 2 through intramolecular Friedel–Crafts hydroarylation of N-aryl propargy...
  
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3. Scheme 2: Strategy towards 2-quinolones 8 bearing a branched substituent on the nitrogen atom.
  
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4. Figure 1: Scope of the protocol.
  
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Beilstein J. Org. Chem. 2018, 14, 2572–2579, doi:10.3762/bjoc.14.234

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New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

Maryna V. Murlykina,
Maryna N. Kornet,
Sergey M. Desenko,
Svetlana V. Shishkina,
Oleg V. Shishkin,
Aleksander A. Brazhko,
Vladimir I. Musatov,
Erik V. Van der Eycken and
Valentin A. Chebanov

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Published 31 May 2017

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1. Graphical Abstract
2. Scheme 1: Aminoazoles in GBB-3CR and Ugi-4CR.
  
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3. Scheme 2: Reactivity of 5-amino-N-aryl-1H-pyrazole-4-carboxamide and 3-amino-5-methylisoxazole in GBB-3CR and...
  
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4. Figure 1: Alternative structures A and B for compounds 4 and 6.
  
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5. Figure 2: Selected data of HSQC and HMBC experiments for compound 4a.
  
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6. Figure 3: Molecular structure of 3-(tert-butylamino)-2-(4-chlorophenyl)-N-(4-fluorophenyl)-1H-imidazo[1,2-b]p...
  
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7. Figure 4: Selected data of NOE and HSQC experiments for compound 9d.
  
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8. Figure 5: Molecular structure of N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-N-(5-methylisoxazol-3-...
  
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Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

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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

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

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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

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

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Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp²)–H activation and C(sp³)–H amination

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

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

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

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