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Type: Artigo de periódico
Title: Arylation Of β,γ-unsaturated Lactones By A Heck-matsuda Reaction: An Unexpected Route To Aryldiazene Butenolides And Pyridazinones
Author: Taylor J.G.
Correia C.R.D.
Abstract: The palladium catalysed coupling of aryldiazonium salts with β-γ-unsaturated lactones under basic conditions has been investigated. Both (3H)-furanone and α-angelicalactone were evaluated as substrates in the Heck Matsuda reaction but both failed to afford the desired arylated butenolides. Under basic conditions, β-γ-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.
Rights: aberto
Identifier DOI: 
Date Issue: 2010
Appears in Collections:Unicamp - Artigos e Outros Documentos

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