REARRANGEMENT OF 3-ETHOXYCARBONYL-5-HYDROXYIMINO-2-METHYL-4-OXONAPHTHO[1,2- b ]FURAN AND 3-ETHOXYCARBONYL-5-HYDROXYIMINO-2-METHYL-4-OXO-1-PHENYLBENZO[ g ]INDOLE BY THE ACTION OF BENZENESULFONYL CHLORIDE IN AN ALKALINE MEDIUM

Abstract

The treatment of 3-ethoxycarbonyl-2-methyl-4,5-dioxonaphtho[1,2- b ]furan 5-monoximes and also the similarly substituted benzo[ g ]indole with benzenesulfonyl chloride in an alkaline medium give 5-(2-cyanophenyl)-3-ethoxycarbonyl-2-methylfuran-4-carboxylic and pyrrole-4-carboxylic acids with high yields as a result of a second-order Beckmann rearrangement. The structures of the initial and final compounds were confirmed by analysis of their mass spectra. Authors: A. P. Stankyavichus, L. M. M. Stankyavichene, and P. B. Terent'ev. English Translation in Chemistry of Heterocyclic Compounds , 1999, 35 (11), pp 1272-1275 http://link.springer.com/article/10.1007/BF02251993