Reaction of Malononitrile and Ethyl Cyanoacetate: a Novel Synthesis of Polyfunctional Pyridine Derivatives

Abstract

Malononitrile reacts with ethyl cyanoacetate to give a polyfunctional substituted pyridine derivative 5. The latter compound reacts with aniline, hydrazines and aromatic aldehydes to give condensated products. The active methylene of 5 couples with benzenediazonium chloride to give the phenylhydrazone derivative which cyclises readily to give a pyrido[2,3-d]pyridazine deriva­tive. 5 reacts with trichloroacetonitrile, and carbon disulphide to give fused heterocyclic deriva­tives.