4.3 Article

Synthesis of heterocycles via alkoxyallenes

Journal

PURE AND APPLIED CHEMISTRY
Volume 82, Issue 9, Pages 1835-1844

Publisher

WALTER DE GRUYTER GMBH
DOI: 10.1351/PAC-CON-09-09-06

Keywords

allenes; carbonyl compounds; imines; multicomponent reactions; natural products; nitriles; palladium-catalyzed reactions

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Lithiated alkoxyallenes are very versatile components for the synthesis of heterocycles such as furans, pyrroles, and 1,2-oxazines, easily allowing the preparation of natural products via these heterocyclic intermediates. A surprising three-component synthesis of N-acylated enaminones allowed the synthesis of highly functionalized 4-hydroxypyridines, 5-acetyloxazoles, and pyrimidines. All these heterocyclic products are ready for further functionalizations, in particular for palladium-catalyzed reactions, leading to libraries of new interesting heterocycles.

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