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2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity. / Sakharov, Pavel A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.

In: Journal of Organic Chemistry, Vol. 83, No. 15, 03.08.2018, p. 8304-8314.

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

Harvard

Sakharov, PA, Novikov, MS & Khlebnikov, AF 2018, '2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity', Journal of Organic Chemistry, vol. 83, no. 15, pp. 8304-8314. https://doi.org/10.1021/acs.joc.8b01004

APA

Sakharov, P. A., Novikov, M. S., & Khlebnikov, A. F. (2018). 2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity. Journal of Organic Chemistry, 83(15), 8304-8314. https://doi.org/10.1021/acs.joc.8b01004

Vancouver

Sakharov PA, Novikov MS, Khlebnikov AF. 2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity. Journal of Organic Chemistry. 2018 Aug 3;83(15):8304-8314. https://doi.org/10.1021/acs.joc.8b01004

Author

Sakharov, Pavel A. ; Novikov, Mikhail S. ; Khlebnikov, Alexander F. / 2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 15. pp. 8304-8314.

BibTeX

@article{dd3953506a8d4123888c06fffd7c244c,
title = "2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity",
abstract = "A synthesis of 2-diazoacetyl-2H-azirines was developed starting from 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles. 2-Diazoacetyl-2H-azirines easily undergo reactions characteristic of α-diazo ketones with preservation of the azirine ring. Reactions with hydrohalogenic, carboxylic, and p-toluenesulfonic acids provide novel 1-(3-aryl-2H-azirin-2-yl)-2-halo- and 2-(R-oxy)ethan-1-ones in good yields. The synthesized 2H-azirines can offer many possibilities for chemical manipulation in heterocyclic synthesis, due to the presence of highly reactive azirine and the exocyclic C(O)-CHN2 or C(O)-CH2X functionalities, which can show orthogonal or domino reactivity. The synthetic usefulness of the developed building blocks was demonstrated by the preparation of new types of heterocyclic dyads (azirine-oxazole, azirine-pyrazoline, azirine-thiazole, azirine-oxirane, pyrrole-oxazole) as well as an azirine chalcone analogue, 2-azidoacetyl-2H-azirine, and 2-diazoacetylaziridine derivatives.",
keywords = "ALPHA,BETA-EPOXY DIAZOMETHYL KETONES, ALPHA-DIAZOCARBONYL COMPOUNDS, IRON-CATALYZED CYCLOPROPANATION, ORGANIC-SYNTHESIS, REARRANGEMENT, CHEMISTRY, HETEROCYCLES, GENERATION, DIAZO",
author = "Sakharov, {Pavel A.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.}",
year = "2018",
month = aug,
day = "3",
doi = "10.1021/acs.joc.8b01004",
language = "English",
volume = "83",
pages = "8304--8314",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "15",

}

RIS

TY - JOUR

T1 - 2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity

AU - Sakharov, Pavel A.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

PY - 2018/8/3

Y1 - 2018/8/3

N2 - A synthesis of 2-diazoacetyl-2H-azirines was developed starting from 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles. 2-Diazoacetyl-2H-azirines easily undergo reactions characteristic of α-diazo ketones with preservation of the azirine ring. Reactions with hydrohalogenic, carboxylic, and p-toluenesulfonic acids provide novel 1-(3-aryl-2H-azirin-2-yl)-2-halo- and 2-(R-oxy)ethan-1-ones in good yields. The synthesized 2H-azirines can offer many possibilities for chemical manipulation in heterocyclic synthesis, due to the presence of highly reactive azirine and the exocyclic C(O)-CHN2 or C(O)-CH2X functionalities, which can show orthogonal or domino reactivity. The synthetic usefulness of the developed building blocks was demonstrated by the preparation of new types of heterocyclic dyads (azirine-oxazole, azirine-pyrazoline, azirine-thiazole, azirine-oxirane, pyrrole-oxazole) as well as an azirine chalcone analogue, 2-azidoacetyl-2H-azirine, and 2-diazoacetylaziridine derivatives.

AB - A synthesis of 2-diazoacetyl-2H-azirines was developed starting from 2H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles. 2-Diazoacetyl-2H-azirines easily undergo reactions characteristic of α-diazo ketones with preservation of the azirine ring. Reactions with hydrohalogenic, carboxylic, and p-toluenesulfonic acids provide novel 1-(3-aryl-2H-azirin-2-yl)-2-halo- and 2-(R-oxy)ethan-1-ones in good yields. The synthesized 2H-azirines can offer many possibilities for chemical manipulation in heterocyclic synthesis, due to the presence of highly reactive azirine and the exocyclic C(O)-CHN2 or C(O)-CH2X functionalities, which can show orthogonal or domino reactivity. The synthetic usefulness of the developed building blocks was demonstrated by the preparation of new types of heterocyclic dyads (azirine-oxazole, azirine-pyrazoline, azirine-thiazole, azirine-oxirane, pyrrole-oxazole) as well as an azirine chalcone analogue, 2-azidoacetyl-2H-azirine, and 2-diazoacetylaziridine derivatives.

KW - ALPHA,BETA-EPOXY DIAZOMETHYL KETONES

KW - ALPHA-DIAZOCARBONYL COMPOUNDS

KW - IRON-CATALYZED CYCLOPROPANATION

KW - ORGANIC-SYNTHESIS

KW - REARRANGEMENT

KW - CHEMISTRY

KW - HETEROCYCLES

KW - GENERATION

KW - DIAZO

UR - http://www.scopus.com/inward/record.url?scp=85049606930&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b01004

DO - 10.1021/acs.joc.8b01004

M3 - Article

AN - SCOPUS:85049606930

VL - 83

SP - 8304

EP - 8314

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -

ID: 34512341