Synthesis, characterization and anti microbial evaluation of novel 1,3,4-oxadiazole containing pyrazolones and 2-thiazolidinone ring systems

P. Nagarjuna Reddy, L. K. Ravi

Abstract

4-(3,6-dioxo-9-(trifluoromethyl)-4-((4-(trifluoromethyl)phenyl)amino)-1-thia-4,7,8-triazaspiro[4,4]non-8-en-7yl)-N-(2-(1-(2- hydrazinyl-2-oxoethyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)-4-oxothiazolidin-3-yl)benzamide were prepared by reflux the ethyl 2-(4-(3-(4-(3,6-dioxo-9-(trifluoromethyl)-4-((4-(trifluoromethyl)phenyl)amino)-1-thia-4,7,8-triazaspiro[4,4]non-8-en- 7yl)benzamido)-4-oxothiazolidin-2-yl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)acetate and hydrazine hydrate afford corresponding 4-(3,6-dioxo-9-(trifluoromethyl)-4-((4-(trifluoromethyl)phenyl)amino)-1-thia-4,7,8-triazaspiro[4,4]non-8-en-7yl)- N-(2-(1-(2-hydrazinyl-2-oxoethyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)-4-oxothiazolidin-3-yl)benzamide.This was subjected to in phosporyl chloride reaction with benzoic acid to give corresponding 4-(3,6-dioxo-9-(trifluoromethyl)-4-((4- (trifluoromethyl)phenyl)amino)-1-thia-4,7,8-triazaspiro[4,4]non-8-en-7yl)-N-(-2-(3-methyl-5-oxo-1-((5-phenyl-1,3,4-oxodiazol- 2-yl)methyl)-4,5-dihydro-1H-pyrazol-4-yl)-4-oxothiazolidin-3-yl)benzamide in excellent yields. The structure of these newly synthesized compounds were characterized by 1HNMR, Mass, IR & Elemental analysis.