Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/54920
Type: Artigo de periódico
Title: ARYLATION OF beta,gamma-UNSATURATED LACTONES BY A HECK-MATSUDA REACTION: AN UNEXPECTED ROUTE TO ARYLDIAZENE BUTENOLIDES AND PYRIDAZINONES
Author: Taylor, JG
Correia, CRD
Abstract: The palladium catalysed coupling of aryldiazonium salts with beta-gamma-unsaturated lactones under basic conditions has been investigated. Both (3H)-furanone and alpha-angelicalactone were evaluated as substrates in the Fleck Matsuda reaction but both failed to afford the desired arylated butenolides. Under basic conditions, beta-gamma-unsaturated lactones generate highly nucleophilic enolates that preferentially undergo azo coupling reactions with arenediazonium salts to afford aryldiazene butenolides. The electronic and steric effect of the substituents on the aryldiazonium salt in the azo coupling reaction is described. Aryldiazene-lactone derivatives were obtained in good yields from a highly facile and straightforward procedure. An aminoisomaleimide was formed from (3H)-furanone and cyclised to the corresponding pyridazinones in modest yield.
Subject: butenolides
azo coupling
Heck-Matsuda
Country: Brasil
Editor: Soc Brasileira Quimica
Rights: aberto
Identifier DOI: 10.1590/S0100-40422010001000012
Date Issue: 2010
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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