Open Access Open Access  Restricted Access Subscription Access

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

Екатерина Е. Галенко, Александр Ф. Хлебников, Михаил С. Новиков
Cover Image

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

 


Keywords


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

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv