New route to N??aryl and N??heteroaryl derivatives of 4??hydroxy??3??quinolinecarboxamides

F Clémence, O Le Martret…

Index: Clemence, Francois; Martret, Odile Le; Collard, Jeannine Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 1345 - 1353

Full Text: HTML

Citation Number: 22

Abstract

Abstract The synthesis of N-aryl and N-heteroaryl substituted 4-hydroxy-3- quinolinecarboxamides 1 is described. The attack of dianions 12 of N-aryl substituted acetamides on the C-4 carbonyl of 4H-3, 1-benzoxazin-4-ones 11 gave rise to ketoamides 13, which smoothly cyclised in the presence of bases to afford quinolinecarboxamides 1. By this method, a large number of 2-substituted 4-hydroxyquinolinecarboxamides can be ...