SYNTHESIS OF NEW FUNCTIONALLY SUBSTITUTED 1-R-TETRAZOLES AND THEIR 5-AMINO DERIVATIVES

Authors

  • С. В. Войтехович Research Institute for Physicochemical Problems, Belorussian State University, Minsk 220080
  • А. Н. Воробьев Research Institute for Physicochemical Problems, Belorussian State University, Minsk 220080
  • П. Н. Гапоник Research Institute for Physicochemical Problems, Belorussian State University, Minsk 220080
  • О. А. Ивашкевич Research Institute for Physicochemical Problems, Belorussian State University, Minsk 220080

DOI:

https://doi.org/10.1007/8214

Keywords:

1-R-5-aminotetrazoles, N-arylcyanamides, 1-R-tetrazoles

Abstract

It has been shown that amino derivatives of sulfanilamide, and also some functionally substituted primary arylamines and cycloalkylamines, undergo heterocyclization with triethyl orthoformate and sodium azide with the formation of 1-monosubstituted tetrazoles. Primary amines of the azole series, 5-aminotetrazole, 5-amino-1-methyltetrazole, 4-amino-1,2,4-triazole, and also less basic arylamines (4-fluoro-3-nitroaniline, 2,6-dibromo-4-nitroaniline) did not react. An efficient method of introducing an amino group into position C(5) of the tetrazole ring of 1-aryltetrazoles is proposed, based on alkaline decomposition of the tetrazole ring and heterocyclization of the resulting N-arylcyanamides on interaction with ammonium azide generated in situ.

How to Cite
Voitekhovich, S. V.; Vorob'ev, A. N.; Gaponik, P. N.; Ivashkevich, O. A.  Chem. Heterocycl. Compd. 2005, 41, 999. [Khim. Geterotsikl. Soedin. 2005, 1174.]

For this article in the English edition, see DOI 10.1007/s10593-005-0267-4


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Published

2023-10-27

Issue

No. 8 (2005)

Section

Original Papers