3-Halo-1-aminoindazoles: An unusual oxidation reaction in chloroform solution

Authors

  • А. Ф. Пожарский Rostov State University, Rostov-on-Don 344090
  • А. А. Антоненко Rostov State University, Rostov-on-Don 344090
  • А. И. Чернышев Rostov State University, Rostov-on-Don 344090
  • Г. Г. Александров Rostov State University, Rostov-on-Don 344090
  • В. B. Кузьменко Rostov State University, Rostov-on-Don 344090
  • B. А. Озерянский Rostov State University, Rostov-on-Don 344090

Abstract

1-Amino-3-chloro-, 1-amino-3-bromo-, and 1-amino-3-iodoindazoles were prepared by reacting hydroxylamine-O-sulfonic acid with 3-haloindazoles in basic medium. It was found that on standing in air in chloroform solutions, these amines undergo a complex transformation which includes the stage of oxidation of a N-amino group, and are slowly converted into 4-(3-haloindazolyl-1)-aminobenzo-1,2,3-triazines. A similar transformation takes place in carbon tetrachloride, but not in toluene or tetrahydrofuran, which suggests that halomethanes participate in the elementary stages of the oxidation reaction.

How to Cite
Pozharskii, A. F.; Antonenko, A. A.; Chernyshev, A. I.; Aleksandrov, G. G.; Kuz'nenko, V. V.; Ozeryanskii, V. A. Chem. Heterocycl. Compd. 1994, 30, 1174. [Khim. Geterotsikl. Soedin. 1994, 1355.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01184880

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Published

1994-10-25

Issue

No. 10 (1994)

Section

Original Papers