Article 2021 · 5 citations

Synthesis, NMR, X-ray crystallography and DFT studies of some regioisomers possessing imidazole heterocycles

Puskullu, Mustafa Orhan, Doganc, Fatima, Ozden, Seckin, Sahin, Ertan, Celik, Ismail, Goker, Hakan

Abstract

Imidazole-containing heterocycles: Imidazopyridines, imidazopyrimidines can exist in several tautomeric forms. Their regioselectivities were determined for N-alkylations with 4-chlorobenzyl bromide under basic conditions (K2CO3) in DMF. We observed that, regioisomers were mainly formed as a mixture in this reaction and N-benzylation occurs at a higher ratio on six membered heterocycles. Their structural assignments were made with the use of two-dimensional H-1-H-1 NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) and H-1-N-15 HMBC (Heteronuclear Multiple Bond Correlation) spectra. Further confirmation of the structure of 2c and 3c were obtained from X-ray crystallography. Experimental data was confirmed by Density Functional Theory (DFT) studies as well. (C) 2021 Elsevier B.V. All rights reserved.

Keywords

Imidazo[4,5-b]pyridine Imidazo[4,5-d]pyrimidine Regioisomer NOESY H-1-N-15 HMBC DFT HMBC NMR DIFFERENTIATION ELUCIDATION

WoS Categories

Chemistry, Physical

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF MOLECULAR STRUCTURE
Year: 2021
Volume: 1243
ISSN: 0022-2860
eISSN: 1872-8014
DOI: 10.1016/j.molstruc.2021.130811
WoS UID: WOS:000688438700011

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