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SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL PYRAZOLES AND OXADIAZOLES DERIVATIVES Synthese und biologische Evaluierung neuartiger PYRAZOLE UND Oxadiazole DERIVATE

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Author(s): Sudhakar Patil and S.S. Bhale

Journal: Heterocyclic Letters
ISSN 2231-3087

Volume: 3;
Issue: 4;
Start page: 519;
Date: 2013;
Original page

Keywords: Pyrimidines | pyrazoles and oxadiazoles etc

ABSTRACT
The Thiocarbonic acid S-(7,7-dimethyl-5-oxo-4-substitured phenyl-1,2,3,4,5,6,7,8- octahydroquinazolin-2-yl)ester-O-ethyl ester (2a-c) was synthesized by reacting compounds (1ac) with ethyl chloroformate in dry acetone at refluxed temperature. Compounds (2a-c) on reaction with hydrazine hydrate in refluxing ethanol afforded respective carbohydrazide (3a-c). The hydrazide (3a-c) was subjected to cyclocondensation with acetyl acetone in dry methanol containing catalytic amount of conc. hydrochloric acid to yield 3-Methyl-5-oxo-4,5-dihydropyrazole- 1-carbothioic acid S-(7,7-dimethyl-5-oxo-4-substituted phenyl-1,2,3,4,5,6,7,8- octahydro-quinazolin-2yl) ester (4a-c). The compound (3a-c) on reaction with carbon disulphide and potassium hydroxide in dry methanol under reflux conditions afforded 7,7-dimethyl-4- substituted phenyl-2-(5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-ylsulfanyl)-2,3,4,6,7,8- hexahydro-1H-quinazolin-5-one.(5a-c). The structures of the compounds were elucidated on the basis of their spectral techniques and also their antimicrobial activity was evaluated against gram positive and gram negative bacteria.
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