Formation of 4-aroylhydrazono-2-methyl- 5-oxo-1-phenyl-3-phenylaminooxalyl-pyrrolidine-2-carboxylates
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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 .
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-1, ester carbonyl group at 1724-1750, amide carbonyl groups at 1684-1705, and ketonic carbonyl group at 1600-1610 cm-1.
The 1 H NMR spectra of compounds 3-6show signals for the aliphatic and aromatic protons and...