Regioselective N-alkylation of some 2 or 6-chlorinated purine analogues
Journal of Molecular Structure, cilt.1272, 2023 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1272
- Basım Tarihi: 2023
- Doi Numarası: 10.1016/j.molstruc.2022.134200
- 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-d]pyrimidine, H-1-N-15 HMBC, NOESY, Regioisomer, DERIVATIVES
- Ankara Üniversitesi Adresli: Evet
Özet
© 2022Imidazopyrimidines have some interconvertible tautomeric forms. Regioselectivities were resolved for N-benzylations of some 8-(substituted phenyl)chloropurines with benzyl or 4-chlorobenzyl bromides under basic conditions (K2CO3) in DMF. It was observed that, while N-benzylation of 2‑chloro-8-(4-substituted)phenylpurines occur on the five-membered imidazole ring (1a, 1b, 2a and 2b) to the contrary, same alkylation reaction of 6‑chloro-8-(4-fluorophenyl)purine (3) occurs on the six-membered pyrimidine ring (4). Their structures were established by combination of 1H–1H NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) and 1H–13C/15N HMBC (Heteronuclear Multiple Bond Correlation) methods. X-ray crystallographic data of compound 4 was also used for further confirmation.