2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity
Publication type: Journal Article
Publication date: 2018-07-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29963871
Organic Chemistry
Abstract
A synthesis of 2-diazoacetyl-2 H-azirines was developed starting from 2 H-azirine-2-carbonyl chlorides, generated by Fe(II)-catalyzed isomerization of 5-chloroisoxazoles. 2-Diazoacetyl-2 H-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-2 H-azirin-2-yl)-2-halo- and 2-(R-oxy)ethan-1-ones in good yields. The synthesized 2 H-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-2 H-azirine, and 2-diazoacetylaziridine derivatives.
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Sakharov P. A., Novikov M. S., Khlebnikov A. F. 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. Vol. 83. No. 15. pp. 8304-8314.
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Sakharov P. A., Novikov M. S., Khlebnikov A. F. 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. Vol. 83. No. 15. pp. 8304-8314.
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TY - JOUR
DO - 10.1021/acs.joc.8b01004
UR - https://pubs.acs.org/doi/10.1021/acs.joc.8b01004
TI - 2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity
T2 - Journal of Organic Chemistry
AU - Sakharov, Pavel A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2018
DA - 2018/07/02
PB - American Chemical Society (ACS)
SP - 8304-8314
IS - 15
VL - 83
PMID - 29963871
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Sakharov,
author = {Pavel A Sakharov and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {2-Diazoacetyl-2 H-azirines: Source of a Variety of 2 H-Azirine Building Blocks with Orthogonal and Domino Reactivity},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.8b01004},
number = {15},
pages = {8304--8314},
doi = {10.1021/acs.joc.8b01004}
}
Cite this
MLA
Copy
Sakharov, Pavel A., et al. “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, Jul. 2018, pp. 8304-8314. https://pubs.acs.org/doi/10.1021/acs.joc.8b01004.