Studies on the Reaction of Quinazoline 3-Oxide with Active Methylene Compound. The Transformation of Quinazoline 3-Oxide into Quinoline Derivatives

Abstract

The reaction of quinazoline 3-oxide (I) with active methylene compound without a base catalyst was carried out and resulted in finding the transformation of I into quinoline derivatives even if the yields of quinoline derivatives were very poor (few percentage). Thus, the reaction with malononitrile gave 2-amino-3-quinolinecarbonitrile (V), with phenylacetonitrile, 2-amino-3-phenylquinoline (VII), with ethyl cyanoacetate, ethyl 2-amino-3-quinolinecarboxylate (IX) and ethyl α-cyano-ο-[N-(2-cyano-2-ethoxycarbonylvinyl) amino] cinnamate (XI), with 1, 3-diphenyl-1, 3-propanedione and 1-phenyl-1, 3-butanedione, 2-phenylquinoline (XII), with 2, 4-pentanedione, methyl 2-methyl-3-quinolyl ketone (XIV) and 4-acetonyl-8-quinolinecarbonitrile (XV), with ethyl acetoacetate, ethyl 2-methyl-3-quinolinecarboxylate (XVII) and 3-acetylcarbostyrile (XVIII), respectively. But in the case of the reaction with diethyl malonate, ethyl 4-quinazolineacetate (XX) was obtained. The possible reaction process for this transformation was also proposed and discussed.