Utility of (p-Sulfonamidophenyl)azomalononitrile, and ethyl acetoacetate in synthesis of fused azole and azines derivatives II

Abstract

[(p-Sulfonamidophenyl)azo]malononitrile (1a,b) reacted with N-cyclohexanemethylidene-2-cyanoacetohydrazide, N'-arylmethylidene-2-cyanoacetohydrazide (3a-c), S-methylthiourea and hydrazine hydrate to afford [1,2,4]triazolo-[1,5-α]pyridinone derivatives (2a,b) & (4a-c), substituted pyrimidines 5a,b and 6a,b. The corresponding pyridazinones 7a,b were synthesized from the reaction of 1c,d with ethyl cyanoacetate. Compound 7a,b reacted with elemental sulfur to yield 8a,b. Compound 6a underwent cycloaddition with α-cinnamonitrile 9a-e to yield 11a-c, 14 and 15. Also, compound 6a reacted with β-ketoester and 1,3-diketones to give 16, 17 and 18.