Advances in 2H-azirine chemistry

A seven-year update

Research outputpeer-review

6 Citations (Scopus)

Abstract

2H-Azirines are versatile building blocks for the preparation of various nitrogen-containing heterocycles. Seven years ago the comprehensive review on azirine chemistry was published in Tetrahedron. Since then, there had been an explosion of research activities in the field of these strained molecules. This renaissance is primarily associated with the discovery of new reactivity of azirines and in particular new catalytic and light-induced reactions, which made possible unusual transformations of this three-membered N-heterocycle into azole and azine derivatives as well as polyheterocyclic systems. The second reason for the progress of azirine chemistry is the development of methods for the preparation of new azirine derivatives. The third reason is the discovery of new synthetic equivalents of azirines, which permitted avoiding the use of unstable azirines in some modern catalytic procedures. In the present comprehensive review, we have placed particular emphasis on discussing the new developments in the synthesis and reactivity of azirines for the period from 2012 until the end of 2018.

Original languageEnglish
Pages (from-to)2555-2624
Number of pages70
JournalTetrahedron
Volume75
Issue number18
DOIs
Publication statusPublished - 3 May 2019

Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Cite this

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title = "Advances in 2H-azirine chemistry: A seven-year update",
abstract = "2H-Azirines are versatile building blocks for the preparation of various nitrogen-containing heterocycles. Seven years ago the comprehensive review on azirine chemistry was published in Tetrahedron. Since then, there had been an explosion of research activities in the field of these strained molecules. This renaissance is primarily associated with the discovery of new reactivity of azirines and in particular new catalytic and light-induced reactions, which made possible unusual transformations of this three-membered N-heterocycle into azole and azine derivatives as well as polyheterocyclic systems. The second reason for the progress of azirine chemistry is the development of methods for the preparation of new azirine derivatives. The third reason is the discovery of new synthetic equivalents of azirines, which permitted avoiding the use of unstable azirines in some modern catalytic procedures. In the present comprehensive review, we have placed particular emphasis on discussing the new developments in the synthesis and reactivity of azirines for the period from 2012 until the end of 2018.",
keywords = "Azirines, Catalysis, Nitrogen heterocycles, Ring expansion, INTERMOLECULAR NITRENE TRANSFER, CATALYZED CASCADE CYCLIZATION, ONE-POT SYNTHESIS, RING-EXPANSION, KETO VINYL AZIDES, BOND FORMATION, C-H FUNCTIONALIZATION, DIELS-ALDER CYCLOADDITIONS, ALPHA-AZIDOCHALCONES, STEREOSELECTIVE-SYNTHESIS",
author = "Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.} and Rostovskii, {Nikolai V.}",
year = "2019",
month = "5",
day = "3",
doi = "10.1016/j.tet.2019.03.040",
language = "English",
volume = "75",
pages = "2555--2624",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "18",

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TY - JOUR

T1 - Advances in 2H-azirine chemistry

T2 - A seven-year update

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

AU - Rostovskii, Nikolai V.

PY - 2019/5/3

Y1 - 2019/5/3

N2 - 2H-Azirines are versatile building blocks for the preparation of various nitrogen-containing heterocycles. Seven years ago the comprehensive review on azirine chemistry was published in Tetrahedron. Since then, there had been an explosion of research activities in the field of these strained molecules. This renaissance is primarily associated with the discovery of new reactivity of azirines and in particular new catalytic and light-induced reactions, which made possible unusual transformations of this three-membered N-heterocycle into azole and azine derivatives as well as polyheterocyclic systems. The second reason for the progress of azirine chemistry is the development of methods for the preparation of new azirine derivatives. The third reason is the discovery of new synthetic equivalents of azirines, which permitted avoiding the use of unstable azirines in some modern catalytic procedures. In the present comprehensive review, we have placed particular emphasis on discussing the new developments in the synthesis and reactivity of azirines for the period from 2012 until the end of 2018.

AB - 2H-Azirines are versatile building blocks for the preparation of various nitrogen-containing heterocycles. Seven years ago the comprehensive review on azirine chemistry was published in Tetrahedron. Since then, there had been an explosion of research activities in the field of these strained molecules. This renaissance is primarily associated with the discovery of new reactivity of azirines and in particular new catalytic and light-induced reactions, which made possible unusual transformations of this three-membered N-heterocycle into azole and azine derivatives as well as polyheterocyclic systems. The second reason for the progress of azirine chemistry is the development of methods for the preparation of new azirine derivatives. The third reason is the discovery of new synthetic equivalents of azirines, which permitted avoiding the use of unstable azirines in some modern catalytic procedures. In the present comprehensive review, we have placed particular emphasis on discussing the new developments in the synthesis and reactivity of azirines for the period from 2012 until the end of 2018.

KW - Azirines

KW - Catalysis

KW - Nitrogen heterocycles

KW - Ring expansion

KW - INTERMOLECULAR NITRENE TRANSFER

KW - CATALYZED CASCADE CYCLIZATION

KW - ONE-POT SYNTHESIS

KW - RING-EXPANSION

KW - KETO VINYL AZIDES

KW - BOND FORMATION

KW - C-H FUNCTIONALIZATION

KW - DIELS-ALDER CYCLOADDITIONS

KW - ALPHA-AZIDOCHALCONES

KW - STEREOSELECTIVE-SYNTHESIS

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U2 - 10.1016/j.tet.2019.03.040

DO - 10.1016/j.tet.2019.03.040

M3 - Article

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JF - Tetrahedron

SN - 0040-4020

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ER -