SYNTHESIS OF SUBSTITUTED 1-(2-METHOXY-5-NITROPHENYL)-5-OXOPYRROLIDINE DERIVATIVES

Abstract

A novel series of 1,3-disubstituted pyrrolidinone derivatives with hydrazone, azole, triazine, and semi- and thiosemicarbazide moieties has been prepared from 1-(2-methoxy-5-nitrophenyl)-5-oxopyrrolidine-3-carbohydrazide. 1-(2-methoxy-5-nitrophenyl)-5-oxopyrrolidine-3-methylcarboxylate was synthesized by esterification of the respective carboxylic acid with an excess (10 times) of methanol under reflux in the presence of a catalytic amount of sulphuric acid. Ester hydrazinolysis at a temperature of 40 °C afforded a corresponding hydrazide. The condensation of hydrazide with aromatic aldehydes gave hydrazone-type derivatives with an azomethine fragment in the molecule. 1-aryl-5-oxopyrrolidine-3-carbohydrazide reacted easily with acetone or ethyl-methylketone under reflux; the corresponding 4-alkylidene-hydrazides were formed. Cyclic compounds – pyrazole, pyrrole, and triazine derivatives – were synthesized by the condensation of hydrazides with diketones 2,4-pentanedione, 2,5-hexanedione and 1,2-diphenyl-1,2-ethanedione, respectively. 2,5-Di-substituted oxadiazole was obtained from the intermediate compound – potassium dithiocarbazate, which was prepared from hydrazide, carbon disulphide, potassium hydroxide in 2-propanol under reflux. Semi- and thiosemicarbazides were synthesized by heating hydrazide with phenylisocyanate or phenylisothiocyanate in methanol. DOI: http://dx.doi.org/10.5755/j01.ct.64.2.6020