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2-AZIDO-5-NITROPYRIMIDINE: SYNTHESIS, MOLECULAR STRUCTURE, AND REACTIONS WITH N-, O-, AND S-NUCLEOPHILES

Е. Б. Горбунов, Р. К. Новикова, П. В. Плеханов, П. А. Слепухин, Г. Л. Русинов, В. Л. Русинов, В. Н. Чарушин, О. Н. Чупахин
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Abstract


We describe the synthesis of 2-azido-5-nitropyrimidine and its azido-tetrazole tautomerism in various solvents and in the crystalline state. It was established that on interacting with N-nucleophiles the attack occurred at the C-2 carbon atom. The O- and S-nucleophiles attacked C-4 position of pyrimidine ring, resulting in tetrazole ring closure.

Authors: E. B. Gorbunov, R. K. Novikova, P. V. Plekhanov, P. A. Slepukhin, G. L. Rusinov, V. L. Rusinov, V. N. Charushin, and O. N. Chupakhin

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (5), pp 766-775

http://link.springer.com/article/10.1007/s10593-013-1308-z


Keywords


2-azido-5-nitropyrimidine; 6-nitrotetrazolo[1,5-a]pyrimidine; azido-tetrazole tautomerism; covalent solvates; nucleophilic addition

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