SYNTHETIC REACTIONS OF COUMARIN-3-(4-AMINOSULFONYL)-CARBANILIDE DERIVATIVES WITH REACTIVE METHYLENE COMPOUNDS

Abstract

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 α–cyano or α–keto group to give pyrido[3,4–c]– and pyrido[3,4–c]–benzo[flcoumarin derivatives 5a, b–11a, b through a nucleophilic addition and cyclization.

Key Words:

• Pyrido–Coumarin Derivatives
• Suflanilamides
• Active Methylenes