Synthesis of Thiazolidinone Related to Pyrroloquinoline Dicarbonitrile

摘要

Reaction of 5,12-diamino-2,6,9,13-tetraoxo-1,2,3,6,6a,8,9,10,13,13a-decahydroindolizino[5,6-g] pyrrolo[ 1,2-a]quinoIine-4,11-dicarbonitrile (2) with different aromatic nitroso compounds (β-nitroso α-naphthol, p-nitroso phenol, p-nitroso N,N-dimethyl aniline) in presence of ethanol and few drops of piperidine catalyst afford the corresponding Schiff bases (3a-c). Also compound 3a was treated with thioglycolic acid in dry benzene and the water formed after heating the reaction mixture by refluxed for 6 h. removed by Dean-Stark apparatus, then benzene removed by distillation, the solid product formed crystallized from ethanol to give compound 4a. Similarly, other compounds 4b and 4c have been synthesized. The structure of compounds 3a-c and 4a-c was demonstrated by elemental analysis, IR, ~1H NMR and ~(13)C NMR spectra and mass spectra.