S 98 Synthesis of acyclic nucleoside analogues by one-step vorbrUggen glyco-sylation of 1,2,4-triazolo[1,5-a]pyrimidine-7-ones [Electronic resource] / I. A. Khalymbadzha, S. L. Deev , T. S. Shestakova, V. L. Rusinov, O. N. Chupakhin // Chimica Techno Acta. - 2015. - Vol. 2, № 2. - С. 158-160. - Bibliogr. : p. 160 (4 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACYCLOVIR Аннотация: New analogues of acyclovir have been prepared by reacting 1,2,4 -triazolo[1,5-a]pyrimidin-7-ones 1а-i and (2-acetoxyethoxy)methyl acetate 2 in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst. The interaction between the compounds 1а-е and 2 has led to a mixture of N3 and N4 isomers. In contrast, the reaction of compounds 1g-i and 2 proceeded selectively to form N3 isomers. In the case of compounds 1a-c the predominant product is the one with the acyclic moiety in azine ring (N4 isomer). Interaction between 1d-f and 2 has led to mixtures comprising mainly N3 isomer. It has been found that the ratio of glycosylation products 1 and 2 are thermodynamically controlled. The structure of the obtained compounds has been proved by 1Н, 13С, two-dimensional 1Н-13С NMR spectroscopy and X-ray analysis. \\\\expert2\\nbo\\Chimica Techno Acta\\2015. V. 2, N 2. P. 158-160.pdf |