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Nouvelles Voies D'Accès Aux Acides Cinnamiques. Application à la Synthèse des Acides O-Méthylthio et O-Méthylsélénocinnamiques Simples et Substitués

✍ Scribed by A. Ruwet; M. Renson

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
633 KB
Volume
79
Category
Article
ISSN
0037-9646

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✦ Synopsis

Abstract

1‐thio‐ and 1‐seleno‐coumarins are synthesized by cyclization of o‐methylthio and o‐methylselenocinnamic acids. The Reformatsky reaction provides a route to cinnamic acids from o‐methylthio and o‐methylselenobenzaldehydes, acetophenones and benzophenones but ethyl bromacetate behaves abnormally owing to SCH~3~ or SeCH~3~; a solution is found by preparing first the organozincic. The Perkin synthesis is also used for benzaldehydes. New methods were investigated from acetophenones and benzophenones: condensation of ethyl cyanacetate and malononitrile with benzylamine as catalyst and condensation with acetonitrile or ethyl acetate and LiNH~2~. Application is given for several o‐methylthio and o‐methylselenocinnamic acids.

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