Константин Ф. Суздалев, С. В. Денькина
Dec 17, 2013
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Chemistry of Heterocyclic Compounds
Abstract
Treatment of indole-3-carbaldehyde with epichlorohydrin gave 1-(oxiran-2-ylmethyl)-1 H -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