DESIGN, SYNTHESIS AND ANTIMICROBIAL EVALUATION OF NOVEL 1-(2-(4-FLUORO BENZYLTHIO)PYRIMIDIN-4-YL-AMINO)-4-(SUBSTITUTED PHENYL)AZETIDIN-2-ONESAbstract
A series of novel 1-(2-(4-fluorobenzylthio)pyrimidin-4-yl-amino)-4-(substituted phenyl)azetidin-2-one analogues (3a-e) were synthesized starting from 2-thiouracil. Reaction of 2-thiouracil with 4-fluorobenzylchloride gave 2-(4-fluorobenzylthio) pyrimidin-4(3H)-one which on chlorination with POCl3 yielded 2-(4-fluorobenzylthio)-4-chloropyrimidine. Further reaction of compound 2-(4-fluorobenzylthio)-4-chloropyrimidine with hydrazine hydrate generated the key intermediate 1-(2-(4-fluorobenzylthio)pyrimidin-4-yl)hydrazine (1). Reaction of compound 1 with appropriate substituted aromatic aldehydes furnished 2-(substituted benzylidene)-1-(2-(4-fluorobenzylthio) pyrimidin-4-yl)hydrazine (2a-e), which on further cyclisation with acetyl chloride in dry benzene furnished 1-(2-(4-fluorobenzylthio)pyrimidin-4-yl-amino)-4-(substituted phenyl) azetidin-2-one analogues (3a-e). Structural assignments of the synthesized compounds were based on their IR, 1H NMR, Mass and analytical data. All the synthesized compounds 3a-e were screened for their preliminary antimicrobial properties. Some of the compounds exhibited promising antimicrobial activities
N. M. Goudgaon* and Y. Rohini Reddy
Department of Post Graduate Studies and Research in Chemistry, Gulbarga University, Gulbarga - 585 106, Karnataka, India.
17 July, 2014
29 September, 2014
01 December, 2014
01 March, 2015