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Paper | Regular issue | Vol 92, No. 6, 2016, pp.1054-1062
Published online, 14th April, 2016
DOI: 10.3987/COM-16-13445
An Efficient Route for Synthesis and Reactions of Seleno-[2, 3-c]coumarin

Shams H. Abdel-Hafez,* Ahmed Elkhateeb, Adel A. Gobouri, Islam H. El Azab, and Gilbert Kirsch

*Department of Chemistry, Faculty of Science, Taif University, Taif-Al-Haweiah 888/21974, Saudi Arabia


Synthesis of new selenium-containing coumarin moiety via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selenium and sodium borohydride gave 3-Cyano-4-coumarinselenol which reacted with different halo-acids, such as chloroacetonitrile, ethyl chloroacetate and chloroacetamide to give the corresponding 3-amino-4-oxo-4H-seleno[3,2-c]chromene-2- derivatives. Hydrazonolysis of the obtained new ethyl 3-amino-4-oxo-4H-seleno[3,2-c] chromene-2-carboxylate afforded the corresponding hydrazino compound. The hydrazino compound was used as a versatile precursor for synthesis of new other heterocyclic compounds containing selenocoumarin moiety. The newly synthesized compounds were characterized using the spectroscopic tools (IR, 1H NMR, 13C NMR and mass spectroscopy) as well as microanalysis.