Synthetic reactions of coumarin-3-(4-aminosulfonyl)-carbanilide derivatives with reactive methylene compounds

Coumarin and benzo[f]coumarin-3-(4-aminosulfonyl)carbanilide derivatives 3a,b react with malononitrile or ethyl cyanoacetate to afford pyrido[3,4-c]- and pyrido[3,4-c]-benzo-[f]coumarin derivatives 4a-d. Compounds 4a-d were also prepared by treatment of arylidene-malononitrile or arylidenecyanoester derivatives 1a-d with ethyl 2-[4-aminosulfonyl carbanilide]acetate 2. 3a,b Derivatives were also allowed to react with a variety of active methylenes having an alpha -cyano or alpha -keto group to give pyrido[3,4-c]- and pyrido[3,4-c]-benzo[f]coumarin derivatives 5a,b-11a,b through a nucleophilic addition and cyclization.