SYNTHETIC ROUTES TOWARDS TETRAZOLIUM AND TRIAZOLIUM DINITROMETHYLIDES

Authors

  • A. R. Katritzky Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida 32611-7200
  • G. L. Sommen Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida 32611-7200
  • A. V. Gromova Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida 32611-7200
  • R. M. Witek Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida 32611-7200
  • P. J. Steel Department of Chemistry, University of Canterbury, Christchurch
  • R. Damavarapu US Army ARDEC, Picatinny Arsenal

DOI:

https://doi.org/10.1007/8411

Keywords:

nitrolic acid, oxadiazole, tetrazolium-5-dinitromethylide sodium salt, X-Ray structure

Abstract

Tetrazolium-5-dinitromethylide sodium salt has been prepared (91%) by cyclization of 1-amino-1-hydrazino-2,2-dinitroethene with  nitrous acid in water. 5-Imino-1-(hydroxy-
iminonitromethyl)-derivatives were obtained by  nitration of 2-(5-amino-1,3-dimethyl-1H-1,2,4-triazol-4-ium-4-yl)- and 2-(5-amino-4-methyl-1H-tetrazolium-1-yl)acetate complex salts. Treatment of 4-methyl-1-(2-oxopropyl)-1-tetrazolium  methylsulfate with nitric and sulfuric acid gave methyl  (3-nitro-1,2,4-oxadiazol-5-yl)amine (27%) probably via dinitromethylide followed by cyclization and loss of nitrogen.

How to Cite
Katritzky, A. R.; Sommen, G. L.; Gromova, A. V.; Witek, R. M.; Steel, P. J.;  Damavarapu, R.  Chem. Heterocycl. Compd. 2005, 41, 111. [Khim. Geterotsikl. Soedin. 2005, 127.]

For this article in the English edition, see DOI 10.1007/s10593-005-0116-5

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Published

2023-12-06

Issue

No. 1 (2005)

Section

Original Papers