Article 2023 · 3 citations

Regioselective <i>N</i>-alkylation of some 2 or 6-chlorinated purine analogues

Doganc, Fatima, Aydin, Amine Sena, Sahin, Ertan, Goker, Hakan

Abstract

Imidazopyrimidines 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 H-1-H-1 NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) and H-1-C-13/N-15 HMBC (Heteronuclear Multiple Bond Correlation) methods. X-ray crystallographic data of compound 4 was also used for further confirmation. (C) 2022 Elsevier B.V. All rights reserved.

Keywords

Imidazo[4,5-d]pyrimidine H-1-N-15 HMBC NOESY Regioisomer DERIVATIVES

WoS Categories

Chemistry, Physical

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF MOLECULAR STRUCTURE
Year: 2023
Volume: 1272
ISSN: 0022-2860
eISSN: 1872-8014
DOI: 10.1016/j.molstruc.2022.134200
WoS UID: WOS:000890356100015

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