Issue 11, 2021

Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products

Abstract

The syntheses and investigations of new biologically active derivatives of dihydropyrimidines by Biginelli reaction in the presence of copper triflate are reported. Due to the fact that salicylaldehyde and its derivatives under Biginelli reaction conditions can lead to the formation of 2 types of dihydropyrimidines, the influence of copper triflate on product formation was also investigated. In addition to this, regioselective oxidation of dihydropyrimidines was performed in the presence of cerium ammonium nitrate and novel oxidized dihydropyrimidines were obtained. Single crystals of some of them were obtained and as a result, the structures of them were investigated by X-ray diffraction method, which allows determining the presence of hydrogen bonds in their structures. In addition to this, the presence of hydrogen bonds in their structures affects the formation of the corresponding tautomer during oxidizing of dihydropyrimidines. Since dihydropyrimidines are claimed to be biologically active compounds, activities of the synthesized compounds were studied against Acinetobacter baumanii, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae and Staphylococcus aureus bacteria.

Graphical abstract: Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
04 12 2020
Accepted
27 1 2021
First published
03 2 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 6312-6329

Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products

A. E. Huseynzada, C. Jelch, H. V. N. Akhundzada, S. Soudani, C. Ben Nasr, A. Israyilova, F. Doria, U. A. Hasanova, R. F. Khankishiyeva and M. Freccero, RSC Adv., 2021, 11, 6312 DOI: 10.1039/D0RA10255E

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