SYNTHESIS OF 1-(OXIRAN-2-YLMETHYL)-1<i>H</i>-INDOLE-3-CARBALDEHYDE AND ITS REACTION WITH ACTIVE METHYLENE COMPOUNDS

Abstract

Treatment of indole-3-carbaldehyde with epichlorohydrin gave 1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde, reaction of which with 1,3-dimethylbarbituric acid or malononitrile gave crotonic condensation products with retention of the oxirane ring. The structure of the reaction products with aroylglycines depends on the conditions. In acetic anhydride a simultaneous formation of an oxazolone ring and bisacylation of the oxirane fragment occurs; the use of ethyl chloroformate in the presence of triethylamine allows to carry out only the heterocyclization process. When treated with the cyclic amines (N-methylpiperazine or morpholine) opening of the oxazolone ring in the products occurs with formation of the corresponding amides.

Authors: K. F. Suzdalev and S. V. Den'kina.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (9), pp 1085-1090

http://link.springer.com/article/10.1007/s10593-011-0878-x