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多卤代烷基取代的色酮、吡喃酮和呋喃酮与水杨醛的反应:通往稠合2H-色烯的直接途径

Reaction of polyhaloalkyl-substituted chromones, pyrones, and furanones with salicylaldehydes as a direct route to fused 2H-chromenes.

作者信息

Sosnovskikh Vyacheslav Ya, Korotaev Vladislav Yu, Chizhov Dmitry L, Kutyashev Igor B, Yachevskii Danil S, Kazheva Olga N, Dyachenko Oleg A, Charushin Valery N

机构信息

Department of Chemistry, Ural State University, 620083 Ekaterinburg, Russian Federation.

出版信息

J Org Chem. 2006 Jun 9;71(12):4538-43. doi: 10.1021/jo060459x.

Abstract

Polyhaloalkyl-substituted chromones, gamma-pyrones, and beta-furanones react with salicylaldehydes in the presence of piperidine to give a wide variety of fused 2H-chromenes in good yields. This novel annulation reaction presumably proceeds by a tandem intermolecular oxa-Michael addition and subsequent intramolecular Mannich condensation.

摘要

多卤代烷基取代的色酮、γ-吡喃酮和β-呋喃酮在哌啶存在下与水杨醛反应,能以良好的产率生成多种稠合的2H-色烯。这种新型的环化反应可能是通过分子间氧杂-Michael加成和随后的分子内曼尼希缩合串联进行的。

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