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

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