REACTIONS OF 4-ARYL-2-HYDRAZINO-3-NITRO-6-R-QUINOLINES WITH HNO<sub>2</sub>

Authors

  • Л. В. Грищук A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • Э. И. Иванов A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • В. Е. Кузьмин A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • А. М. Турянская A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • Р. Ю. Иванова A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080

Keywords:

hydrazinoquinolines, oxadiazoloquinolines, tetrazoloquinolines, quinolines, ring-chain (azidotetrazole) tautomerism

Abstract

The reaction of 4-aryl-2-hydrazino-3-nitro-6-R-quinolines with NaNO2 in AcOH gives the corresponding tetrazolo[1,5-a]quinolines. In contrast to tetrazolo[1,5-c]pyrimidines they cannot be converted to 6-R-4-phenyl[1,2,5]oxadiazolo[3,4-b]quinoline-3-oxides by heating in THF, toluene, or AcOH. Total energy quantum-chemical calculations using the MINDO/3 and MNDO methods show that [1,2,5]oxadiazolo[3,4-b]quinoline-3-oxides are significantly higher in energy (230-280 kcal/mol) than the mentioned tetrazolo[1,5-a]quinolines and hence their formation is unlikely.

How to Cite
Grishchuk, L. V.; Ivanov, E. I.; Kuz'min, V. E.; Turyanskaya, A. M.; Ivanova, R. Yu. Chem. Heterocycl. Compd. 2003, 39, 340. [Khim. Geterotsikl. Soedin. 2003, 384.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1023966827299

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Published

2003-03-25

Issue

No. 3 (2003)

Section

Original Papers