Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN 2′-SN 2′ Cascade Mechanism
Publication type: Journal Article
Publication date: 2018-10-10
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30335384
Organic Chemistry
Abstract
An effective and operationally simple method for the preparation of methyl 2-(di/tri/tetraazol-1-yl)-2 H-azirine-2-carboxylates from accessible methyl 2-halo-2 H-azirine-2-carboxylates and NH-azoles has been developed. The azoles having enhanced NH acidity, react with 2-halo-2 H-azirines in the presence of Et3N in a deprotonated form, while the azoles having highly nucleophilic sp2 nitrogen react in neutral form. According to the DFT calculations, the substitution of the halogen by the azole proceeds via an SN2'-SN2' cascade, with the initial conjugate substitution of the halogen being the rate-determining step. The formation of 2,3-dipyrazolylaziridines in the reaction of pyrazole provides experimental evidence for the cascade mechanism of the reaction.
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Total citations:
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Citations from 2024:
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(52.94%)
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GOST
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Agafonova A. V. et al. Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism // Journal of Organic Chemistry. 2018. Vol. 83. No. 21. pp. 13473-13480.
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Agafonova A. V., Rostovskii N. V., Smetanin I. A., Starova G. L., Khlebnikov A. F., Novikov M. S. Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism // Journal of Organic Chemistry. 2018. Vol. 83. No. 21. pp. 13473-13480.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.8b02295
UR - https://pubs.acs.org/doi/10.1021/acs.joc.8b02295
TI - Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism
T2 - Journal of Organic Chemistry
AU - Agafonova, Anastasiya V
AU - Rostovskii, Nikolai V
AU - Smetanin, Ilia A
AU - Starova, G. L.
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2018
DA - 2018/10/10
PB - American Chemical Society (ACS)
SP - 13473-13480
IS - 21
VL - 83
PMID - 30335384
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2018_Agafonova,
author = {Anastasiya V Agafonova and Nikolai V Rostovskii and Ilia A Smetanin and G. L. Starova and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.8b02295},
number = {21},
pages = {13473--13480},
doi = {10.1021/acs.joc.8b02295}
}
Cite this
MLA
Copy
Agafonova, Anastasiya V., et al. “Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism.” Journal of Organic Chemistry, vol. 83, no. 21, Oct. 2018, pp. 13473-13480. https://pubs.acs.org/doi/10.1021/acs.joc.8b02295.