On the Reaction of Quinazoline with Active Methylene Compound

Abstract

The reaction of quinazoline (I) with active methylene compound in the presence of sodium amide were carried out and resulted in the formation of 4, 4'-biquinazoline (III) and 4-substituted quinazoline. Thus reaction with phenylacetonitrile gave III and α-phenyl-4-quinazolineacetonitrile (IV), with ethyl cyanoacetate, III and methyl α-cyano-4-quinazolineacetate (V), with nitromethane, III and 4-(nitromethyl) quinazoline (VI), respectively. But in the case of the reaction with malononitrile, it gave III, 2-amino-3-quinolinecarbonitrile (VII) and 2-amino-6-methoxy-3, 5-pyridinedicarbonitrile (VIII). The reaction of I with active methylene compound without a base catalyst was also carried out and succeeded in finding the transformation of I into quinoline derivatives. Thus, the reaction with malononitrile gave VII, with ethyl cyanoacetate, ethyl 2-amino-3-quinolinecarboxylate (XV) and 2-hydroxy-3-quinolinecarbonitrile (XVI), with phenyl-acetonitrile, 2-amino-3-phenylquinoline, respectively. But in the case of the reaction with diethyl malonate, ethyl 4-quinazolineacetate (XVIII) was obtained.