Chemistry of Heterocyclic Compounds

, volume 52 , issue 9 , pages 637-650

Isoxazole-azirine isomerization as a reactivity switch in the synthesis of heterocycles

Ekaterina E Galenko ¹

Alexander F Khlebnikov ¹

Mikhail S. Novikov ¹

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Institute of Chemistry, Saint Petersburg State University, Saint Petersburg, Russia |

Publication type: Journal Article

Publication date: 2016-09-01

Springer Nature

Chemistry of Heterocyclic Compounds

scimago Q4

wos Q4

SJR: 0.243

CiteScore: 2.7

Impact factor: 1.0

ISSN: 00093122, 15738353

DOI: 10.1007/s10593-016-1944-1

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Organic Chemistry

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 performed. A total of 76 references are given.

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Galenko E. E., Khlebnikov A. F., Novikov M. S. Isoxazole-azirine isomerization as a reactivity switch in the synthesis of heterocycles // Chemistry of Heterocyclic Compounds. 2016. Vol. 52. No. 9. pp. 637-650.

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RIS Copy

TY - JOUR

DO - 10.1007/s10593-016-1944-1

UR - https://doi.org/10.1007/s10593-016-1944-1

TI - Isoxazole-azirine isomerization as a reactivity switch in the synthesis of heterocycles

T2 - Chemistry of Heterocyclic Compounds

AU - Galenko, Ekaterina E

AU - Khlebnikov, Alexander F

AU - Novikov, Mikhail S.

PY - 2016

DA - 2016/09/01

PB - Springer Nature

SP - 637-650

IS - 9

VL - 52

SN - 0009-3122

SN - 1573-8353

ER -

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@article{2016_Galenko,

author = {Ekaterina E Galenko and Alexander F Khlebnikov and Mikhail S. Novikov},

title = {Isoxazole-azirine isomerization as a reactivity switch in the synthesis of heterocycles},

journal = {Chemistry of Heterocyclic Compounds},

year = {2016},

volume = {52},

publisher = {Springer Nature},

month = {sep},

url = {https://doi.org/10.1007/s10593-016-1944-1},

number = {9},

pages = {637--650},

doi = {10.1007/s10593-016-1944-1}

}

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Galenko, Ekaterina E., et al. “Isoxazole-azirine isomerization as a reactivity switch in the synthesis of heterocycles.” Chemistry of Heterocyclic Compounds, vol. 52, no. 9, Sep. 2016, pp. 637-650. https://doi.org/10.1007/s10593-016-1944-1.