An efficient regioselective synthesis of N-alkylated purine-triazole analogues

Pandit, Chintan ; Pandya, Mayank ; Kapadiya, Khushal ; Jadeja, Yashwantsinh ; Gohel, Jyoti

Abstract

Nitrogen rich purine adduct (2) was prepared by reaction of 2,6-dichloro purine (1) with hydrazine hydrate was converted to hybrid purine-triazole ring (4) by a simple cyclisation process (con. HCl & methanol) on reaction with
3-phenoxy benzaldehyde. The regioselectivity of synthesized adducts was carried out by simple spectroscopic techniques i.e. IR, 1H NMR & 13C NMR spectra. These studies gave an idea regarding replacement of chlorine out of C-2 or C-6 position. Novelty was introduced by alkyl substation at N-9 position of imidazole ring and at –NH of triazole ring and a series of 4-chloro-5a,6-dihydro-1,6-dialkylated-8-(3-phenoxyphenyl)-1H-[1,2,4]triazolo[3,4-e]purine (5a-5g) hybrids were synthesized.


Keyword(s)

2,6-Dichloropurine, triazoles, regioselectivity

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