Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid

Condensation of ethyl 4-formyl-3,5-dimethyl-1 H -pyrrole-2-carboxylate with various aromatic amines and with 5-amino-3-(4-bromo- phenyl(tolyl))-1 H -pyrazole in absolute boiling ethanol afforded new azomethines as Schiff bases. The structure and E -configuration of the azomethine fragment were detec...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2023-07, Vol.59 (6-7), p.449-455
Main Authors: Mikhedkina, Olena I., Ananieva, Valeriia V., Sakhno, Yana I., Melnyk, Igor I., Vereshchak, Vladyslav O., Osolodchenko, Tetiana P., Shishkina, Svitlana V., Tsygankov, Alexander V., Chebanov, Valentyn A.
Format: Article
Language:English
Subjects:
Amines
Aromatic amines
Biological activity
Chemistry
Chemistry and Materials Science
Ethanol
Imines
NMR spectroscopy
Nuclear magnetic resonance spectroscopy
Organic Chemistry
Pharmacy
Pyrazole
Schiff bases
Toluene
X ray analysis
Zinc chloride
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Summary:Condensation of ethyl 4-formyl-3,5-dimethyl-1 H -pyrrole-2-carboxylate with various aromatic amines and with 5-amino-3-(4-bromo- phenyl(tolyl))-1 H -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 1 H 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 ZnCl 2 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)-1 H -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-1 H -pyrrole-2-carboxylate exhibited the highest antibacterial activity.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03215-w