Synthesis of α-aryl enaminones through reactions of β-aryl enones with benzyl azide

TETRAHEDRON LETTERS

卷:53

Article

Cunha, Silvio¹ 

[1] Univ Fed Bahia, Inst Quim, BR-40170290 Salvador, BA, Brazil

关键词: Enaminones;    Benzalacetones;    1,2-Aryl migration;    1,3-Dipolar reaction;    Benzylidene acetones;   

DOI  :  10.1016/j.tetlet.2012.09.125

来源: Elsevier

【 摘 要 】

Reaction of benzalacetones and dibenzalacetones with benzyl azide promoted by BF3 center dot OEt2 afforded Z and E densely substituted acyclic alpha-aryl enaminones in 21-95% yield. For benzalacetones major Z-isomers were obtained, while E-isomers were the tendency for dibenzalacetones. The synthesis involves domino 1,3-dipolar cycloaddition and 1,2-aryl migration, and is the first metal free practical alternative to the preparation of acyclic alpha-aryl enaminones from commercial available or easily prepared starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

Free