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AZOMETHINES BASED ON ETHYL 4-FORMYL-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE, ITS BIOLOGICAL ACTIVITY AND REACTION WITH THIOGLYCOLIC ACID

Olena I. Mikhedkina, Valeriia V. Ananieva, Yana I. Sakhno, Igor I. Melnyk, Vladyslav O. Vereshchak, Tetiana P. Osolodchenko, Svitlana V. Shishkina, Alexander V. Tsygankov, Valentyn A. Chebanov
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Abstract


Condensation of ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate with various aromatic amines and with 5-amino-3-(4-bromophenyl(tolyl))-1H-pyrazole in absolute boiling ethanol afforded new azomethines as Schiff bases. The structure and E-configuration of the azomethine fragment were detected by the methods of 1H NMR spectroscopy and X-ray analysis. Reaction of these compounds with thioglycolic acid in toluene, DMF, or AcOH at reflux with or without the addition of ZnCl2 as well as under microwave irradiation had an unusual pathway leading to the formation of ethyl 3,5-dimethyl-4-(5-oxo-1,3-oxathiolan-2-yl)-1H-pyrrole-2-carboxylate exclusively. The obtained azomethines were found to be effective only against Gram positive bacteria, whereas ethyl 4-{(E)-[(4-chlorophenyl)imino]methyl}-3,5-dimethyl-1H-pyrrole-2-carboxylate exhibited the highest antibacterial activity.

Keywords


5-aminopyrazole; azomethine; 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate; pyrrole derivative; biological activity.

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