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4 article(s) from Zimmer, Reinhold

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

Tilman Lechel,
Roopender Kumar,
Mrinal K. Bera,
Reinhold Zimmer and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

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Graphical Abstract

Scheme 1: Discovery of the LANCA three-component reaction. The reaction of pivalonitrile (1) with lithiated m...

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Scheme 2: Proposed mechanism of the LANCA three-component reaction to β-ketoenamides KE and pyridin-4-ol deri...

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Scheme 3: One-pot preparation of pyridin-4-ols PY and their subsequent transformations to highly substituted ...

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Scheme 4: Synthesis of β-ketoenamides KE by the LANCA three-component reaction of alkoxyallenes, nitriles and...

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Scheme 5: β-Ketoenamides KE36–43 derived from enantiopure components.

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Scheme 6: Bis-β-ketoenamides KE44–46 derived from aromatic dicarboxylic acids.

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Scheme 7: Conversion of alkyl propargyl ethers E into aryl-substituted β-ketoenamides KEAr and selected produ...

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Scheme 8: Condensation of LANCA-derived β-ketoenamides KE with ammonium salts to give 5-alkoxy-substituted py...

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Scheme 9: Synthesis of PM31–35 from β-ketoenamides KE37, KE38, KE40, KE41 and KE78 obtained by method A (NH₄O...

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Scheme 10: Synthesis of bis-pyrimidine derivatives PM36, PM39 and PM40 from β-ketoenamides KE44–46 by method A...

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Scheme 11: Functionalization of pyrimidine derivatives PM through selenium dioxide oxidations of PM5, PM9, PM15...

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Scheme 12: Conversion of 2-vinyl-substituted pyrimidine PM7 into aldehyde PM50; (NMO = N-methylmorpholine N-ox...

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Scheme 13: Deprotection of 5-alkoxy-substituted pyrimidines PM2, PM20 and PM29 and conversion into nonaflates ...

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Scheme 14: Palladium-catalyzed coupling reactions of PM54 and PM12 giving rise to new pyrimidine derivatives P...

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Scheme 15: Synthesis of pyrimidyl-substituted pyridyl nonaflate PM60.

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Scheme 16: Condensation of LANCA-derived β-ketoenamides KE with hydroxylamine hydrochloride leading to pyrimid...

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Scheme 17: Reactions of β-ketoenamides KE15 and KE7 with hydroxylamine hydrochloride leading to pyrimidine N-o...

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Scheme 18: Structures of pyrimidine N-oxides PO30–33 derived from β-ketoenamides KE43, KE45, KE78 and KE80.

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Scheme 19: Reduction of PO4 to PM5 and Boekelheide rearrangements of PO13, PO14, PO4 and PO30 to 4-acetoxymeth...

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Scheme 20: Deprotection of 4-acetoxymethyl-substituted pyrimidine derivatives PM61 and PM63, oxidations to for...

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Scheme 21: Synthesis of pyrimidinyl-substituted alkyne PM74 and conversion into furopyrimidine PM75 and Sonoga...

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Scheme 22: Trifluoroacetic acid-promoted conversion of LANCA-derived β-ketoenamides KE into oxazoles OX and 1,...

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Scheme 23: Conversion of β-ketoenamide KE79 into oxazole OX16 and transformation into 5-styryl-substituted oxa...

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Scheme 24: Mechanisms of the formation of 1,2-diketones DK and of acetyl-substituted oxazole derivatives OX.

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Scheme 25: Hydrogenolyses of benzyloxy-substituted β-ketoenamides KE52 and KE54 to 1,2-diketone DK14 and to di...

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Scheme 26: Conversions of 2,4-dicyclopropyl-substituted oxazole OX7 into oxazole derivatives OX18–20 (PPA = po...

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Scheme 27: Syntheses of vinyl and ethynyl-substituted oxazole derivatives OX21 and OX23 and their palladium-ca...

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Scheme 28: Synthesis of C₃-symmetric oxazole derivative OX28 and the STM current image of its 1-phenyloctane s...

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Scheme 29: Condensation of 1,2-diketones DK with o-phenylenediamine to quinoxalines QU1–7 (CAN = cerium ammoni...

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Scheme 30: The LANCA three-component reaction leading to β-ketoenamides KE and the structure of functionalized...

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Review

Published 13 Mar 2019

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Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

Michal Medvecký,
Igor Linder,
Luise Schefzig,
Hans-Ulrich Reissig and
Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

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Scheme 1: Access to enantiopure 3,6-dihydro-1,2-oxazines 3 via lithiated alkoxyallenes 1 and carbohydrate-der...

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Scheme 2: Iodination of 1,2-oxazines syn-3a–c and anti-3a,d leading to 5-iodo-substituted 1,2-oxazines syn-4a...

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Scheme 3: Sonogashira reactions of 4-methoxy-1,2-oxazines syn-4a, anti-4a and anti-4d leading to 5-alkynyl-su...

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Scheme 4: Sonogashira reactions of D-glyceraldehyde-derived 1,2-oxazines syn-4a–c leading to 5-alkynyl-substi...

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Scheme 5: Heck reactions of 1,2-oxazine syn-4a leading to 5-alkenyl-substituted 1,2-oxazines syn-13, syn-14 a...

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Scheme 6: Suzuki–Miyaura reactions of 1,2-oxazines syn-4a, syn-4b and anti-4d leading to 5-styryl-substituted...

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Scheme 7: Cross-coupling reaction of 1,2-oxazine anti-4d leading to 5-cyano-substituted 1,2-oxazine anti-25.

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Scheme 8: Desilylation of 1,2-oxazine syn-5 and subsequent click reaction with benzyl azide leading to 5-(1,2...

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Scheme 9: Hydrogenation of 1,2-oxazine syn-21 leading to γ-amino alcohols 27a,b and subsequent ring closure t...

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Scheme 10: Hydrogenation of 1,2-oxazine anti-24 to products anti-29 and anti-30.

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Full Research Paper

Published 29 Dec 2016

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Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups

Jakub Saadi,
Christoph Bentz,
Kai Redies,
Dieter Lentz,
Reinhold Zimmer and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1236–1242, doi:10.3762/bjoc.12.118

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Scheme 1: Planned Heck reaction of A to compound B and serendipitous discovery of the palladium-catalyzed cyc...

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Scheme 2: Synthesis of compounds A (1–6) via methyl 2-siloxycyclopropanecarboxylates D, their alkylation to E...

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Scheme 3: Palladium-catalyzed reactions of methyl ketone 1 to tetralin derivative 7 and of isopropyl-substitu...

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Scheme 4: Palladium-catalyzed cyclization of diastereomeric cyclopentanone derivatives 3a/3b to products 11a ...

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Figure 1: Molecular structure (ORTEP, [14]) of compound 12a (thermal ellipsoids at 50% probability).

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Scheme 5: Palladium-catalyzed cyclizations of diastereomeric cyclohexanone derivatives 4a and 4b leading ster...

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Figure 2: Molecular structure (ORTEP, [14]) of compound 14a (thermal ellipsoids at 50% probability).

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Scheme 6: Palladium-catalyzed cyclizations of cycloheptanone derivatives 5a and 5b leading to products 15a an...

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Figure 3: Molecular structure (ORTEP, [14]) of compound 15a (thermal ellipsoids at 50% probability).

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Figure 4: Molecular structure (ORTEP [14]) of compound 15b (thermal ellipsoids at 50% probability).

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Scheme 7: Palladium-catalyzed cyclization of p-methoxy-substituted aryl iodide 6a/6b to compound 16.

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Scheme 8: Typical palladium-catalyzed cyclization of an o-iodoaniline derivative to a tricyclic tertiary alco...

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Scheme 9: Proposed transition state (TS) explaining the stereoselective formation of cyclization products.

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Scheme 10: Possible mechanism of the reduction of palladium(II) to palladium(0) by triethylamine (additional l...

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Full Research Paper

Published 16 Jun 2016

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Palladium- catalyzed cross coupling reactions of 4-bromo- 6H-1,2-oxazines

Reinhold Zimmer,
Elmar Schmidt,
Michal Andrä,
Marcel-Antoine Duhs,
Igor Linder and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2009, 5, No. 44, doi:10.3762/bjoc.5.44

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Graphical Abstract

Scheme 1: Brominations of 6H-1,2-oxazines. a) Br₂, Et₂O, −30 °C, 2 h. b) Et₃N, −30 °C to r.t., overnight.

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Scheme 2: Chlorinations of 6H-1,2-oxazines. a) Cl₂, Et₂O, −30 °C. b) Et₃N, −30 °C to r.t.

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Scheme 3: Suzuki-couplings of 4-bromo-6H-1,2-oxazines. a) ArB(OH)₂, Pd(PPh₃)₄, Na₂CO₃, toluene, 80 °C, 3 h.

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Scheme 4: Sonogashira-couplings of 4-bromo-6H-1,2-oxazines. a) PdCl₂(PPh₃)₂, CuI, Et₃N, toluene, r.t., 6–20 h....

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Scheme 5: Sonogashira-couplings of 4,5-dibromo-6H-1,2-oxazines. a) PdCl₂(PPh₃)₂, CuI, Et₃N, toluene, r.t., 4 ...

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Scheme 6: Preparation of trisubstituted pyridine derivatives: a) BF₃·OEt₂, CH₂Cl₂, −78 °C to r.t., overnight.

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Preliminary Communication

Published 16 Sep 2009

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