Naslov
Conjugates of 1,2,3-triazoles and acyclic pyrimidine nucleoside analogues: syntheses and X-ray crystallographic studies

Autori
Korunda, Silvija ; Krištafor, Svjetlana ; Cetina, Mario ; Raić-Malić, Silvana

Izvornik
Current organic chemistry (1385-2728) 17 (2013), 10; 1114-1124

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
acyclic pyrimidine nucleoside ; azide-alkyne cycloaddition ; click chemistry ; 1, 4-disubstituted 1, 2, 3-triazoles ; X-ray diffraction ; supramolecular assembling

Sažetak
The synthesis of novel acyclic pyrimidine nucleoside analogues with 1, 2, 3-triazole ring bound via ethylene spacer or directly to C-5 of pyrimidine ring has been reported. 1, 4- Disubstituted 1, 2, 3-triazoles were synthesized by click chemistry approach using regioselective copper(I)-catalyzed 1, 3-dipolar cycloaddition reaction between terminal alkyne and azido pyrimidines under both conventional (method A) and microwave (method B) conditions. N-Alkylation of triazolyl pyrimidines afforded 5-[2-(1, 2, 3- triazolyl)ethyl]pyrimidine derivatives with penciclovir-, ganciclovir-like and 2, 3- dihydroxypropyl side chain, as well as 5-(1, 2, 3- triazolyl)pyrimidine derivatives with penciclovir- and ganciclovir-like side chain. The stereostructures of 2-hydroxyethyl, 2- tosyloxyethyl, 2-azidoethyl and 4-acetoxymethyl- 1, 2, 3-triazolyl C-5 substituted pyrimidine derivatives were unambiguously confirmed by their X-ray crystal structure analysis.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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