Reaction of Isatin-1-acetamides with Alkoxides: Synthesis of Novel 1,4-Dihydro-3-hydroxy-4-oxo-2-quinolinecarboxamides

Abstract

The study of the reactivity of a series of isatin-1-acet-amides with hot alkoxides is described. These reactions lead to 1,4-dihydro-3-hydroxy-4-oxo-2-quinolinecarboxamides as main products, and 3-hydroxy-2-oxindoles as well as other minor products. Experimental results indicate that the starting compounds undergo transformation through two principal routes: ring expansion of isa-tin leading to quinoline carboxamides, probably as the result of a ring-opening and ring-closure rearrangement, and reduction of the keto carbonyl group due to the reductive ability of alkoxides.