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.
