New routes to polyfunctionally substituted pyridine, pyridopyridine, quinoline, and pyridazine derivatives

Abstract

Abstract The pyridine derivatives 4 and 10 are obtained by condensing β‐aminocrotononitrile ( 1a ) with malononitrile. Compound 4 affords the pyridylpyridazine 7 on coupling with aryldiazonium salts. The reaction of 1a with cyanothioacetamide affords 12 which affords the thieno[2,3‐ b ]pyridine 13 on treatment with phenacylbromide, and pyrido[2,3‐ b ]pyridine 15 on treatment with benzylidenemalononitrile ( 14 ). A variety of new pyridines, cyclohexadiene, and pyridopyridine derivatives were obtained from reaction of 2‐amino‐1‐propene‐1,1,3‐tricarbonitrille ( 1b ) and diethyl 3‐amino‐2‐cyanopent‐2‐enedioate ( 1c ) with Michael ‐systems. Reaction of 1b with acrylonitrile afforded an acyclic diadduct 25 which could be cyclized to the aminoquinoline 26 .