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Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads. / Mikhailov, Kirill I.; Galenko, Ekaterina E.; Galenko, Alexey V.; Novikov, Mikhail S.; Ivanov, Alexander Yu.; Starova, Galina L.; Khlebnikov, Alexander F.

In: Journal of Organic Chemistry, Vol. 83, No. 6, 16.03.2018, p. 3177-3187.

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

Harvard

Mikhailov, KI, Galenko, EE, Galenko, AV, Novikov, MS, Ivanov, AY, Starova, GL & Khlebnikov, AF 2018, 'Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads', Journal of Organic Chemistry, vol. 83, no. 6, pp. 3177-3187. https://doi.org/10.1021/acs.joc.8b00069

APA

Mikhailov, K. I., Galenko, E. E., Galenko, A. V., Novikov, M. S., Ivanov, A. Y., Starova, G. L., & Khlebnikov, A. F. (2018). Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads. Journal of Organic Chemistry, 83(6), 3177-3187. https://doi.org/10.1021/acs.joc.8b00069

Vancouver

Mikhailov KI, Galenko EE, Galenko AV, Novikov MS, Ivanov AY, Starova GL et al. Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads. Journal of Organic Chemistry. 2018 Mar 16;83(6):3177-3187. https://doi.org/10.1021/acs.joc.8b00069

Author

Mikhailov, Kirill I. ; Galenko, Ekaterina E. ; Galenko, Alexey V. ; Novikov, Mikhail S. ; Ivanov, Alexander Yu. ; Starova, Galina L. ; Khlebnikov, Alexander F. / Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 6. pp. 3177-3187.

BibTeX

@article{e83e65bbf167450191f5c31457d49137,
title = "Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads",
abstract = "2-(1H-Pyrazol-1-ylcarbony1)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360-410 nm with high quantum yields.",
keywords = "ISOXAZOLES, COMPLEXES, CHEMISTRY, REACTIVITY, OXIDATION, CATALYSTS, AZIRINES, ROUTES, AGENTS",
author = "Mikhailov, {Kirill I.} and Galenko, {Ekaterina E.} and Galenko, {Alexey V.} and Novikov, {Mikhail S.} and Ivanov, {Alexander Yu.} and Starova, {Galina L.} and Khlebnikov, {Alexander F.}",
year = "2018",
month = mar,
day = "16",
doi = "10.1021/acs.joc.8b00069",
language = "Английский",
volume = "83",
pages = "3177--3187",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "6",

}

RIS

TY - JOUR

T1 - Fe(II)-Catalyzed Isomerization of 5-Chloroisoxazoles to 2H-Azirine-2-carbonyl Chlorides as a Key Stage in the Synthesis of Pyrazole-Nitrogen Heterocycle Dyads

AU - Mikhailov, Kirill I.

AU - Galenko, Ekaterina E.

AU - Galenko, Alexey V.

AU - Novikov, Mikhail S.

AU - Ivanov, Alexander Yu.

AU - Starova, Galina L.

AU - Khlebnikov, Alexander F.

PY - 2018/3/16

Y1 - 2018/3/16

N2 - 2-(1H-Pyrazol-1-ylcarbony1)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360-410 nm with high quantum yields.

AB - 2-(1H-Pyrazol-1-ylcarbony1)-2H-azirines were synthesized by in situ trapping of 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles, with pyrazoles. According to DFT calculations, the selectivity of nucleophilic substitution at the carbonyl group of 2H-azirine-2-carbonyl chloride by a pyrazole nucleophile, which is a mixture of two tautomers, is controlled by thermodynamic factors. 2-(1H-Pyrazol-1-ylcarbonyl)-2H-azirines are excellent precursors for the preparation of two other pyrazole nitrogen heterocycle dyads: 5-(1H-pyrazol-1-yl)oxazoles by photolysis and 1-(1H-pyrrol-2-ylcarbonyl)-1H-pyrazoles by a Ni(II)-catalyzed reaction with 1,3-dicarbonyl compounds. 5-(1H-Pyrazol-1-yl)oxazoles show strong emission in acetonitrile at 360-410 nm with high quantum yields.

KW - ISOXAZOLES

KW - COMPLEXES

KW - CHEMISTRY

KW - REACTIVITY

KW - OXIDATION

KW - CATALYSTS

KW - AZIRINES

KW - ROUTES

KW - AGENTS

UR - http://www.scopus.com/inward/record.url?scp=85044101979&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/feiicatalyzed-isomerization-5chloroisoxazoles-2-h-azirine2carbonyl-chlorides-key-stage-synthesis-pyr

U2 - 10.1021/acs.joc.8b00069

DO - 10.1021/acs.joc.8b00069

M3 - статья

VL - 83

SP - 3177

EP - 3187

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 6

ER -

ID: 28186183