PARTIALLY HYDROGENATED AROMATIC SUBSTITUTED TETRAZOLO[1,5-<i>a</i>]PYRIMIDINES

Authors

  • C. М. Десенко V. N. Karazin National University, Kharkov 61077
  • E. C. Глaдков V. N. Karazin National University, Kharkov 61077
  • C. A. Комыхов V. N. Karazin National University, Kharkov 61077
  • О. В. Шишкин NTK "Institute of Monocrystals", Kharkov 61001
  • В. Д. Орлов V. N. Karazin National University, Kharkov 61077

Keywords:

5-aminotetrazole, dihydrotetrazolo[1,5-a]pyrimidines, α,β-unsaturated ketones, tetrahydrotetrazolo[1,5-a]pyrimidines, molecular structure, rearrangement, cyclocondensation

Abstract

By treating 5-aminotetrazole with aromatic a,b-unsaturated ketones or with Mannich base hydrochlorides there have been synthesized aromatic substituted 4,7-dihydrotetrazolo[1,5-a]-pyrimidines. They can be reduced to the corresponding 4,5,6,7-tetrahydro derivatives by the action of NaBH4. The high thermodynamic stability of the 4,7-dihydrotetrazolo[1,5-a]pyrimidines when compared with the 4,5-dihydro isomers has been revealed. Reaction of 5-aminotetrazole both with cyclohexanone as well as with 2-cyclohexylidenecyclohexanone leads to formation of 9,9‑pentamethylene-4,5,6,7,8,9-hexahydrotetrazolo[5,1-b]quinazoline, the structure of which was demonstrated using X-ray crystallography.

How to Cite
Desenko, S. M.; Gladkov, E. S.; Komykhov, S. A.; Shishkin, O. V.; Orlov, V. D. Chem. Heterocycl. Compd. 2001, 37, 747. [Khim. Geterotsikl. Soedin. 2001, 811.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1011925631511

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Published

2001-06-25

Issue

No. 6 (2001)

Section

Original Papers