beta-(2-Aminophenyl)-alpha,beta-ynones readily react with nitrogen nucleophiles to give three major types of products, depending on reaction conditions and variation in the nucleophiles. The reaction may lead to simple 1,2-nucleophilic adducts or, at higher temperatures, to a divergent sequential cyclisation giving rise to 2-aryl-4-aminoquinolines by reaction with amines, or to substituted 2-aryl or 2-alkyl-4-alkylidene quinazolines by reaction with amidines. The latter could also be synthesised by reaction of beta-(2-aminophenyl)-alpha,beta-ynones with iminochlorides.
Divergent sequential reactions of alpha,beta-(2-aminophenyl)-alpha,beta-ynones with nitrogen nucleophiles
ARCADI, Antonio
2004-01-01
Abstract
beta-(2-Aminophenyl)-alpha,beta-ynones readily react with nitrogen nucleophiles to give three major types of products, depending on reaction conditions and variation in the nucleophiles. The reaction may lead to simple 1,2-nucleophilic adducts or, at higher temperatures, to a divergent sequential cyclisation giving rise to 2-aryl-4-aminoquinolines by reaction with amines, or to substituted 2-aryl or 2-alkyl-4-alkylidene quinazolines by reaction with amidines. The latter could also be synthesised by reaction of beta-(2-aminophenyl)-alpha,beta-ynones with iminochlorides.File in questo prodotto:
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