Alkylation of 5-dimethylaminotetrazolo-[1,5-a][1,3,5]triazin-7-one

作者：Bakharev Vladimir V^*; Parfenov Victor E; Gidaspov Alexander A; Pimenov Andrey A; Slepukhin Pavel A; Suponitsky Kyrill Yu

来源：Chemistry of Heterocyclic Compounds, 2015, 51(8): 745-748.

DOI：10.1007/s10593-015-1768-4

• tetrazolo[1,5-a][1,3,5]triazines
• alkylation
• ambident nucleophiles
• anomalous nucleosides
• tetrazolylguanidines

Reaction of 5-dimethylaminotetrazolo[1,5-D degrees][1,3,5]triazin-7-one tetrabutylammonium salt with allyl bromide in acetonitrile proceeds with the formation of 3-allyl-5-dimethylaminotetrazolo[1,5-a][1,3,5]triazin-7-one (N-alkylation), 6-allyloxy-4-azido-N,N-dimethyl-1,3,5-triazin-2-amine (O-alkylation), and 2-(1-allyl-1H-tetrazol-5-yl)-1,1-dimethylguanidine as the product of hydrolysis of N-alkylated tetrazolo[1,5-a][1,3,5]triazin-7-one. The structure of the reaction products was confirmed by IR, H-1 and C-13 NMR spectroscopy as well as elemental and X-ray structural analysis data.

• 出版日期2015-8