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oai:ojs.www.eurjchem.com:article/500 2012-03-31T06:42:44Z eurjchem:ART driver

Cyclocondensation, antimicrobial activity and semi-empirical AM1-MO calculations of benzopyrone derivatives El-Shaaer, Hafez Mohamed Synthesis Benzopyrone 4-Quinolinone Cyclocondensation AM1-MO calculation Antimicrobial activity An efficient synthesis of 7-amino-9-hydroxy-6-oxo-6H-benzo[c]chromene-8-carbonitrile derivatives (2,6) and 4-methyl-2-oxo-2H-chromene-3-carbonitrile (5) via Claisen condensation of 2-hydroxyacetophenones (1,3) with ethyl cyanoacetate in the presence of sodium metal is reported. Reaction of 5 with thiosemicarbazide gave 1-(3-cyano-4-methyl-2-oxoquinolin-1(2H)-yl)thiourea (7). Treatment of 5 with 6,8-dichloro-4-oxo-4H-chromene-3-carboxaldehyde gave 4-(2-(6,8-dichloro-4-oxo-4H-chromen-3-yl)-2-hydroxyethyl)-2-oxo-2H-chromene-3-carbonitrile (9). Further treatment of 5 with ethyl acetate followed by condensation with 6,8-dichloro-3-formylchromone gave 7-((6,8-dichloro-4-oxo-4H-chromen-3-yl)methyleneamino)-9-hydroxy-6H-benzo[c]chromen-6-one (12). Structures of the products were established on the basis of elemental analysis, IR, 1H and 13C NMR, mass spectra and semi-empirical AM1-MO calculations. The antimicrobial activities of the synthesized products were also studied. Atlanta Publishing House LLC 2012-03-31 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/500 10.5155/eurjchem.3.1.51-56.500 European Journal of Chemistry; Vol. 3 No. 1 (2012): March 2012; 51-56 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/500/PDF