Synthesis, NMR, X-ray crystallography and DFT studies of some regioisomers possessing imidazole heterocycles
JOURNAL OF MOLECULAR STRUCTURE, cilt.1243, 2021 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1243
- Basım Tarihi: 2021
- Doi Numarası: 10.1016/j.molstruc.2021.130811
- Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
- Anahtar Kelimeler: Imidazo[4,5-b]pyridine, Imidazo[4,5-d]pyrimidine, Regioisomer, NOESY, H-1-N-15 HMBC, DFT, HMBC NMR, DIFFERENTIATION, ELUCIDATION
- Atatürk Üniversitesi Adresli: Evet
Özet
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.