V. L. Gein, R. O. Dyrenkov, N. A. Kornienko
Apr 11, 2012
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Chemistry of Heterocyclic Compounds
Abstract
The reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with benzoic acid hydrazide has previously been studied, and the structure of the compound obtained was confirmed by X-ray structural analysis [1]. We have for the first time studied the reaction of a pyrrole-2,3-dione ring annelated to a pyrroline ring (compounds 1, 2) with benzoic acid hydrazides. The reaction with said reagents proceeds when refluxed in acetonitrile over 3-5 min to give the 4-aroylhydrazono-2-methyl-5-oxo-1-phenyl-3-phenylaminooxalylpyrrolidine-2-carboxylates 3-6. The compounds 3-6 obtained are yellow, crystalline substances soluble in DMF and DMSO, but also in less polar organic solvents when heated. The IR spectra of compounds 3-6 show stretching bands for the N–H bonds at 3290-3355 cm, ester carbonyl group at 1724-1750, amide carbonyl groups at 1684-1705, and ketonic carbonyl group at 1600-1610 cm. The H NMR spectra of compounds 3-6 show signals for the aliphatic and aromatic protons and also the presence of the arylhydrazide fragment NH group proton singlet at 10.67-10.83 and an amide fragment NH group proton singlet at 11.23-11.44 ppm. The mass spectrum of compound 5 shows the presence of a molecular ion peak with m/z 526 and fragment ions confirming its structure. To establish the steric structure of compounds 3-6 the monocrystal of compound 4 was obtained by slow crystallization from acetonitrile and its X-ray structural analysis was performed (Fig. 1).