SYNTHESIS OF ISOXAZOLE AND AZOLE ENSEMBLES BASED ON 1,3-DIPOLAR CYCLOADDITION REACTION OF ENAMINES WITH NITRILE OXIDES

Authors

  • Илья В. Ефимов Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg 620002
  • Юрий М. Шафран Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg 620002
  • Наталья Н. Волкова Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg 620002
  • Николай А. Беляев Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg 620002
  • Павел А. Слепухин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi St., Yekaterinburg 620137
  • Василий А. Бакулев Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg 620002

DOI:

https://doi.org/10.1007/3417

Keywords:

enamines, hydroxamoyl chlorides, isoxazoles, cycloaddition, regioselectivity

Abstract

2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to the formation of the isoxazole ring.

Authors: Ilya V. Efimov, Yuri M. Shafran, Natalya N. Volkova, Nikolay A. Belyaev, Pavel A. Slepukhin, Vasiliy A. Bakulev*

 

Author Biography

Василий А. Бакулев, Ural Federal University named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg 620002

Заведующий кафедрой Технологии органического синтеза

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Published

2016-10-11

Issue

Vol. 52 No. 9 (2016): Pericyclic reactions in heterocyclic chemistry

Section

Original Papers