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Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution : Evidence for an SN2′-SN2′ Cascade Mechanism. / Agafonova, Anastasiya V.; Rostovskii, Nikolai V.; Smetanin, Ilia A.; Starova, Galina L.; Starova, Galina L.; Novikov, Mikhail S.

In: Journal of Organic Chemistry, Vol. 83, No. 21, 02.11.2018, p. 13473-13480.

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

Harvard

Agafonova, AV, Rostovskii, NV, Smetanin, IA, Starova, GL, Starova, GL & Novikov, MS 2018, '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, pp. 13473-13480. https://doi.org/10.1021/acs.joc.8b02295

APA

Agafonova, A. V., Rostovskii, N. V., Smetanin, I. A., Starova, G. L., Starova, G. L., & Novikov, M. S. (2018). 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, 83(21), 13473-13480. https://doi.org/10.1021/acs.joc.8b02295

Vancouver

Agafonova AV, Rostovskii NV, Smetanin IA, Starova GL, Starova GL, Novikov MS. 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 Nov 2;83(21):13473-13480. https://doi.org/10.1021/acs.joc.8b02295

Author

Agafonova, Anastasiya V. ; Rostovskii, Nikolai V. ; Smetanin, Ilia A. ; Starova, Galina L. ; Starova, Galina L. ; Novikov, Mikhail S. / Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution : Evidence for an SN2′-SN2′ Cascade Mechanism. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 21. pp. 13473-13480.

BibTeX

@article{92640dade0584e0b8b725d594e448ed2,
title = "Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism",
abstract = "An effective and operationally simple method for the preparation of methyl 2-(di/tri/tetraazol-1-yl)-2H-azirine-2-carboxylates from accessible methyl 2-halo-2H-azirine-2-carboxylates and NH-azoles has been developed. The azoles having enhanced NH acidity, react with 2-halo-2H-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.",
author = "Agafonova, {Anastasiya V.} and Rostovskii, {Nikolai V.} and Smetanin, {Ilia A.} and Starova, {Galina L.} and Starova, {Galina L.} and Novikov, {Mikhail S.}",
year = "2018",
month = nov,
day = "2",
doi = "10.1021/acs.joc.8b02295",
language = "English",
volume = "83",
pages = "13473--13480",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "21",

}

RIS

TY - JOUR

T1 - Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution

T2 - Evidence for an SN2′-SN2′ Cascade Mechanism

AU - Agafonova, Anastasiya V.

AU - Rostovskii, Nikolai V.

AU - Smetanin, Ilia A.

AU - Starova, Galina L.

AU - Starova, Galina L.

AU - Novikov, Mikhail S.

PY - 2018/11/2

Y1 - 2018/11/2

N2 - An effective and operationally simple method for the preparation of methyl 2-(di/tri/tetraazol-1-yl)-2H-azirine-2-carboxylates from accessible methyl 2-halo-2H-azirine-2-carboxylates and NH-azoles has been developed. The azoles having enhanced NH acidity, react with 2-halo-2H-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.

AB - An effective and operationally simple method for the preparation of methyl 2-(di/tri/tetraazol-1-yl)-2H-azirine-2-carboxylates from accessible methyl 2-halo-2H-azirine-2-carboxylates and NH-azoles has been developed. The azoles having enhanced NH acidity, react with 2-halo-2H-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.

UR - http://www.scopus.com/inward/record.url?scp=85055324152&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02295

DO - 10.1021/acs.joc.8b02295

M3 - Article

C2 - 30335384

AN - SCOPUS:85055324152

VL - 83

SP - 13473

EP - 13480

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -

ID: 35810675