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

Authors

  • Е. Б. Горбунов I. Ya. Postovskii Institute of Organic Synthesis
  • Р. К. Новикова I. Ya. Postovskii Institute of Organic Synthesis
  • П. В. Плеханов I. Ya. Postovskii Institute of Organic Synthesis
  • П. А. Слепухин I. Ya. Postovskii Institute of Organic Synthesis
  • Г. Л. Русинов I. Ya. Postovskii Institute of Organic Synthesis
  • В. Л. Русинов I. Ya. Postovskii Institute of Organic Synthesis
  • В. Н. Чарушин I. Ya. Postovskii Institute of Organic Synthesis
  • О. Н. Чупахин I. Ya. Postovskii Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/620

Keywords:

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

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

Downloads

Published

2013-05-17

Issue

No. 5 (2013)

Section

Original Papers