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 b-(2-aminophenyl)-a,b-ynones with iminochlorides. q 2004 Elsevier
Divergent sequential reactions of beta-(2-aminophenyl)-alpha,beta-ynones with nitrogen nucleophiles / E. Rossi, G. Abbiati, V. Canevari, D. Nava, A. Arcadi. - In: TETRAHEDRON. - ISSN 0040-4020. - 60:50(2004 Dec 06), pp. 11391-11398. [10.1016/j.tet.2004.09.082]
Divergent sequential reactions of beta-(2-aminophenyl)-alpha,beta-ynones with nitrogen nucleophiles
E. RossiPrimo
;G. AbbiatiSecondo
;V. Canevari;D. NavaPenultimo
;
2004
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 b-(2-aminophenyl)-a,b-ynones with iminochlorides. q 2004 ElsevierPubblicazioni consigliate
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