Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate

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Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate. / Agafonova, Anastasiya V.; Smetanin, Ilia A.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

In: Chemistry of Heterocyclic Compounds, Vol. 53, No. 10, 01.10.2017, p. 1068-1071.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{fa95587a5a6843e3bb0644008d9db661,

title = "Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate",

abstract = "[Figure not available: see fulltext.] N,N-Dialkylamides and esters of 2-(chloro/bromo/iodo)-2H-azirine-2-carboxylic acids were synthesized by isomerization of 4-halo-5-(dialkylamino/alkoxy)isoxazoles in the presence of catalytic amounts of FeSO4·7H2O. The use of iron(II) sulfate as catalyst, compared to its chloride, provides the advantage of avoiding halide exchange products in isomerization reactions of 4-bromo- and 4-iodoisoxazoles, as well as prevents catalyst deactivation by the 5-amino substituent of isoxazole, compared to rhodium(II) carboxylates.",

keywords = "2Н-azirines, catalysis, halogenated heterocycles, iron(II) salts, isoxazoles, rearrangements",

author = "Agafonova, {Anastasiya V.} and Smetanin, {Ilia A.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",

year = "2017",

month = oct,

day = "1",

doi = "10.1007/s10593-017-2172-z",

language = "English",

volume = "53",

pages = "1068--1071",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer Nature",

number = "10",

}

RIS

TY - JOUR

T1 - Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate

AU - Agafonova, Anastasiya V.

AU - Smetanin, Ilia A.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2017/10/1

Y1 - 2017/10/1

N2 - [Figure not available: see fulltext.] N,N-Dialkylamides and esters of 2-(chloro/bromo/iodo)-2H-azirine-2-carboxylic acids were synthesized by isomerization of 4-halo-5-(dialkylamino/alkoxy)isoxazoles in the presence of catalytic amounts of FeSO4·7H2O. The use of iron(II) sulfate as catalyst, compared to its chloride, provides the advantage of avoiding halide exchange products in isomerization reactions of 4-bromo- and 4-iodoisoxazoles, as well as prevents catalyst deactivation by the 5-amino substituent of isoxazole, compared to rhodium(II) carboxylates.

AB - [Figure not available: see fulltext.] N,N-Dialkylamides and esters of 2-(chloro/bromo/iodo)-2H-azirine-2-carboxylic acids were synthesized by isomerization of 4-halo-5-(dialkylamino/alkoxy)isoxazoles in the presence of catalytic amounts of FeSO4·7H2O. The use of iron(II) sulfate as catalyst, compared to its chloride, provides the advantage of avoiding halide exchange products in isomerization reactions of 4-bromo- and 4-iodoisoxazoles, as well as prevents catalyst deactivation by the 5-amino substituent of isoxazole, compared to rhodium(II) carboxylates.

KW - 2Н-azirines

KW - catalysis

KW - halogenated heterocycles

KW - iron(II) salts

KW - isoxazoles

KW - rearrangements

UR - http://www.scopus.com/inward/record.url?scp=85038034404&partnerID=8YFLogxK

U2 - 10.1007/s10593-017-2172-z

DO - 10.1007/s10593-017-2172-z

M3 - Article

AN - SCOPUS:85038034404

VL - 53

SP - 1068

EP - 1071

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 10

ER -

ID: 13392497