Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2H-azirines

Research output

18 Citations (Scopus)

Abstract

A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.

Original languageEnglish
Pages (from-to)4478-4488
Number of pages11
JournalSynthesis (Germany)
Volume49
Issue number19
DOIs
Publication statusPublished - 2017

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Azirines
Isoxazoles
Isomerization
Amides
Esters
Metals
Rhodium
Carboxylic Acids
Carboxylic acids
Catalysis
Catalysts

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

@article{7ad4b6d3f17a4fbeadfe249c6f666c9c,
title = "Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2H-azirines",
abstract = "A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.",
keywords = "azirines, catalysis, haloheterocycles, iron(II) chloride, isomerization, isoxazoles, rhodium(II) carboxylates",
author = "Rostovskii, {Nikolai V.} and Agafonova, {Anastasiya V.} and Smetanin, {Ilia A.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.} and Ruvinskaya, {Julia O.} and Starova, {Galina L.}",
year = "2017",
doi = "10.1055/s-0036-1590822",
language = "English",
volume = "49",
pages = "4478--4488",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "19",

}

TY - JOUR

T1 - Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2H-azirines

AU - Rostovskii, Nikolai V.

AU - Agafonova, Anastasiya V.

AU - Smetanin, Ilia A.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

AU - Ruvinskaya, Julia O.

AU - Starova, Galina L.

PY - 2017

Y1 - 2017

N2 - A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.

AB - A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.

KW - azirines

KW - catalysis

KW - haloheterocycles

KW - iron(II) chloride

KW - isomerization

KW - isoxazoles

KW - rhodium(II) carboxylates

UR - http://www.scopus.com/inward/record.url?scp=85027080681&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1590822

DO - 10.1055/s-0036-1590822

M3 - Article

AN - SCOPUS:85027080681

VL - 49

SP - 4478

EP - 4488

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 19

ER -