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Paper | Regular issue | Vol 36, No. 5, 1993, pp.947-959
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6079
Synthesis and Reactions of Some 3-Cyano-4-methylcoumarins

Hassan M. F. Madkour

*Department of Chemistry, Faculty of Science, Ain Shams University, Abbassiya 11566, Cairo, Egypt

Abstract

O-Hydroxy ketones (I) were converted into 3-cyano-4-methylcoumarins (II) via condensation with ethyl cyanoacetate in presence of piperidine or ammonium acetate as a catalyst. The behavior of compound (II) towards Grignard and Michael reactions was investigated. The reactions of 3-acetylcoumarin (III) with hydrazines under different conditions were carried out to give the hydrazone (VI a), phenylhydrazone (IV b) and pyrazole (V) derivatives. Also, the 4-styryl derivatives (VI) were obtained by condensation of II with different aromatic and heterocyclic aldehydes. A one pot synthesis of Michael product (VII) from the reaction of VI with malononitrile was described.