ISOXAZOLE-AZIRINE ISOMERIZATION AS A REACTIVITY SWITCH IN THE SYNTHESIS OF HETEROCYCLES

Authors

  • Екатерина Е. Галенко Chemistry Institute of St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034
  • Александр Ф. Хлебников Chemistry Institute of St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034
  • Михаил С. Новиков Chemistry Institute of St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034

DOI:

https://doi.org/10.1007/3207

Keywords:

azirine, heterocycles, isoxazole, isomerization, catalysis, pericyclic reactions, radical reactions, photoisomerization, 1, 5-electrocyclization

Abstract

This review contains a generalized and systematically arranged data about thermal, photochemical, and catalytic transformations of isoxazole-2-carbonyl-2H-azirine that were published in the period from 1969 to 2015, and considers the possibilities for using these compounds in the synthesis of nitrogen heterocycles. Radical and pericyclic steps of isomerization reactions have been discussed. Density functional theory calculations of the relative thermodynamic stability of isomeric isoxazoles and azirines have been peformed. A total of 76 references are given.

Authors: Yekaterina E. Galenko, Alexander F. Khlebnikov*, Mikhail S. Novikov

 

Author Biographies

Екатерина Е. Галенко, Chemistry Institute of St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034

Институт химии

Александр Ф. Хлебников, Chemistry Institute of St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034

Институт химии

Михаил С. Новиков, Chemistry Institute of St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg 199034

Институт химии

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Published

2016-06-17

Issue

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

Section

Review Articles