Abstract
Alkynones are versatile three-carbon building blocks in heterocyclic chemistry. They are easily and efficiently prepared by a modified Sonogashira coupling of acid chlorides and terminal alkynes. As a consequence of the mild reaction conditions the stage is set for new diversity-oriented routes to heterocycles by sequential and consecutive transformations. Hence, isoxazoles, indolizines, pyrazoles, pyridimines, 1,5-benzoheteroazepines, furans, oxazoles, pyrroles, tetrahydro- β-carbolines, 4H-thiochromen-4-ones and 4H-thiopyrano[2,3-b]pyridin-4-ones are readily accessible by multicomponent coupling-cycloaddition, coupling-addition-cyclocondensation, or coupling-addition-substitution reactions in a one-pot fashion.
Current Organic Chemistry
Title: Multi-component Heterocycle Syntheses via Catalytic Generation of Alkynones
Volume: 13 Issue: 18
Author(s): Benjamin Willy and Thomas J. J. Muller
Affiliation:
Abstract: Alkynones are versatile three-carbon building blocks in heterocyclic chemistry. They are easily and efficiently prepared by a modified Sonogashira coupling of acid chlorides and terminal alkynes. As a consequence of the mild reaction conditions the stage is set for new diversity-oriented routes to heterocycles by sequential and consecutive transformations. Hence, isoxazoles, indolizines, pyrazoles, pyridimines, 1,5-benzoheteroazepines, furans, oxazoles, pyrroles, tetrahydro- β-carbolines, 4H-thiochromen-4-ones and 4H-thiopyrano[2,3-b]pyridin-4-ones are readily accessible by multicomponent coupling-cycloaddition, coupling-addition-cyclocondensation, or coupling-addition-substitution reactions in a one-pot fashion.
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Cite this article as:
Willy Benjamin and Muller J. J. Thomas, Multi-component Heterocycle Syntheses via Catalytic Generation of Alkynones, Current Organic Chemistry 2009; 13 (18) . https://dx.doi.org/10.2174/138527209789630479
DOI https://dx.doi.org/10.2174/138527209789630479 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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