Successful utilization of $$\upbeta $$ β -ketonitrile in Biginelli reaction: synthesis of 5-cyanodihydropyrimidine

Abstract

A Biginelli reaction of β-ketonitriles, aldehydes and urea in principle can yield 5-cyano substituted dihydropyrimidinones. Although potentially very useful, this substituted heterocycle is often difficult to synthesize via the three component reaction, presumably due to the lack of stability of β-ketonitriles. The present work describes the development of reaction conditions yielding the desired product. Interesting mechanistic observations have also been noted. Thirteen new compounds (derivatives) of 5-cyanodihydropyrimidin were synthesized.