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2 article(s) from Lechel, Tilman

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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Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

Tilman Lechel,
Irene Brüdgam and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, No. 42, doi:10.3762/bjoc.6.42

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Graphical Abstract

Scheme 1: Deprotection of 3-alkoxypyridinols 1 to pyridine-3,4-diols 2. ^aMethod a: Pd/C, H₂, MeOH, rt, 1 d; ^b...

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Figure 1: X-ray crystal structure of compound 2c/2c′.

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Scheme 2: Conversion of pyridine-3,4-diols 2 into pyridinediyl bistriflates or -nonaflates 3. a) Et₃N, Rf₂O, ...

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Scheme 3: Sonogashira couplings of pyridinediyl bis(perfluoroalkanesulfonates) 3. a) Pd(PPh₃)₄ [or Pd(OAc)₂/P...

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Figure 2: Absorption and fluorescence spectra of compounds 4b and 4c.

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Published 29 Apr 2010

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