REACTIONS OF MALONOTHIOAMIDE DERIVATIVES WITH AZIDES

Authors

  • Л. Н. Дианова Ural Federal University named after the First President of Russia B. N. Yeltsin
  • В. С. Берсенева Ural Federal University named after the First President of Russia B. N. Yeltsin
  • О. С. Ельцов Ural Federal University named after the First President of Russia B. N. Yeltsin
  • Ж.-Д. Фан State Laboratory of Heteroorganic Chemistry, Nankai University
  • В. А. Бакулев Ural Federal University named after the First President of Russia B. N. Yeltsin

DOI:

https://doi.org/10.1007/1758

Keywords:

aryl azides, malonothioamides, 1, 2, 3-thiadiazoles, 3-triazoles, cyclocondensation, rearrangements

Abstract

The reactions of primary and tertiary malonothioamides with aryl and sulfonyl azides can take place in three directions, depending on the nature of the thioamides and azides. Ethoxycarbonylthioacetamide reacts with aryl azides with the formation of ethyl 5-amino-1-aryl-1,2,3-triazole-4-carboxylates. In reaction with aryl azides tertiary thioamides of cyanoacetic acid form 5-amino-1-aryl-1,2,3-triazole-4‑carbothioamides, and in reaction with tosyl azide they form 5-amino-4-carboxamidino-1,2,3-thiadiazoles. Hypothetical mechanisms for the transformations are discussed.

How to Cite
Dianova, L. N.; Berseneva, V. S.; El'tsov, O. S.; Fan, Z.-J.; Bakulev, V. A. Chem. Heterocycl. Compd. 2014, 50, 972. [Khim. Geterotsikl. Soedin. 2014, 1055.]

For this article in the English edition see DOI 10.1007/s10593-014-1552-x

Author Biographies

Л. Н. Дианова, Ural Federal University named after the First President of Russia B. N. Yeltsin

Лидия Николаевна Дианова

ученый секретарь ГАК

В. С. Берсенева, Ural Federal University named after the First President of Russia B. N. Yeltsin

Вера Сергеевна Берсенева

доцент кафедры Технологии органического синтеза

О. С. Ельцов, Ural Federal University named after the First President of Russia B. N. Yeltsin

Олег Станиславович Ельцов

доцент кафедры ТОС

Ж.-Д. Фан, State Laboratory of Heteroorganic Chemistry, Nankai University

профессор Нанкайского университета

В. А. Бакулев, Ural Federal University named after the First President of Russia B. N. Yeltsin

Василий Алексеевич Бакулев

Заведующий кафедрой Технологии органического синтеза

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Published

2014-07-25

Issue

No. 7 (2014)

Section

Original Papers