Standard

Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles. / Агафонова, Анастасия Викторовна; Павленко, Юлия Игоревна; Сахаров, Павел Алексеевич; Сметанин, Илья Алексеевич; Хлебников, Александр Феодосиевич; Крюкова, Мария Александровна; Новиков, Михаил Сергеевич.

In: Journal of Organic Chemistry, Vol. 89, No. 9, 17.04.2024, p. 6281–6291.

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

Harvard

Агафонова, АВ, Павленко, ЮИ, Сахаров, ПА, Сметанин, ИА, Хлебников, АФ, Крюкова, МА & Новиков, МС 2024, 'Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles', Journal of Organic Chemistry, vol. 89, no. 9, pp. 6281–6291. https://doi.org/10.1021/acs.joc.4c00264

APA

Агафонова, А. В., Павленко, Ю. И., Сахаров, П. А., Сметанин, И. А., Хлебников, А. Ф., Крюкова, М. А., & Новиков, М. С. (2024). Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles. Journal of Organic Chemistry, 89(9), 6281–6291. https://doi.org/10.1021/acs.joc.4c00264

Vancouver

Агафонова АВ, Павленко ЮИ, Сахаров ПА, Сметанин ИА, Хлебников АФ, Крюкова МА et al. Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles. Journal of Organic Chemistry. 2024 Apr 17;89(9):6281–6291. https://doi.org/10.1021/acs.joc.4c00264

Author

Агафонова, Анастасия Викторовна ; Павленко, Юлия Игоревна ; Сахаров, Павел Алексеевич ; Сметанин, Илья Алексеевич ; Хлебников, Александр Феодосиевич ; Крюкова, Мария Александровна ; Новиков, Михаил Сергеевич. / Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles. In: Journal of Organic Chemistry. 2024 ; Vol. 89, No. 9. pp. 6281–6291.

BibTeX

@article{a44ba022c92c48bc8509f6305a529736,
title = "Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles",
abstract = "An efficient protocol for the synthesis of stable 2-azaallyl anion salts by the reaction of alkyl 2-bromo-2H-azirine-2-carboxylates with trimethylsilyl cyanide/Bu4NF has been developed. The domino reaction proceeds in four steps via the cleavage of the azirine C-C bond to provide the tetrabutylammonium salts of stereochemically pure 2-azaallyl anions having U-configuration relative to the cyano groups. The anions with an ortho-substituted aryl group or styryl group exist as a mixture of two geometrical isomers across the N2-C3 bond. 2-Azaallyl anion salts have been shown to be convenient substrates for the one-pot synthesis of densely functionalized 2H-pyrroles by the alkylation-cyclization sequence.",
author = "Агафонова, {Анастасия Викторовна} and Павленко, {Юлия Игоревна} and Сахаров, {Павел Алексеевич} and Сметанин, {Илья Алексеевич} and Хлебников, {Александр Феодосиевич} and Крюкова, {Мария Александровна} and Новиков, {Михаил Сергеевич}",
year = "2024",
month = apr,
day = "17",
doi = "10.1021/acs.joc.4c00264",
language = "English",
volume = "89",
pages = "6281–6291",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "9",

}

RIS

TY - JOUR

T1 - Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles

AU - Агафонова, Анастасия Викторовна

AU - Павленко, Юлия Игоревна

AU - Сахаров, Павел Алексеевич

AU - Сметанин, Илья Алексеевич

AU - Хлебников, Александр Феодосиевич

AU - Крюкова, Мария Александровна

AU - Новиков, Михаил Сергеевич

PY - 2024/4/17

Y1 - 2024/4/17

N2 - An efficient protocol for the synthesis of stable 2-azaallyl anion salts by the reaction of alkyl 2-bromo-2H-azirine-2-carboxylates with trimethylsilyl cyanide/Bu4NF has been developed. The domino reaction proceeds in four steps via the cleavage of the azirine C-C bond to provide the tetrabutylammonium salts of stereochemically pure 2-azaallyl anions having U-configuration relative to the cyano groups. The anions with an ortho-substituted aryl group or styryl group exist as a mixture of two geometrical isomers across the N2-C3 bond. 2-Azaallyl anion salts have been shown to be convenient substrates for the one-pot synthesis of densely functionalized 2H-pyrroles by the alkylation-cyclization sequence.

AB - An efficient protocol for the synthesis of stable 2-azaallyl anion salts by the reaction of alkyl 2-bromo-2H-azirine-2-carboxylates with trimethylsilyl cyanide/Bu4NF has been developed. The domino reaction proceeds in four steps via the cleavage of the azirine C-C bond to provide the tetrabutylammonium salts of stereochemically pure 2-azaallyl anions having U-configuration relative to the cyano groups. The anions with an ortho-substituted aryl group or styryl group exist as a mixture of two geometrical isomers across the N2-C3 bond. 2-Azaallyl anion salts have been shown to be convenient substrates for the one-pot synthesis of densely functionalized 2H-pyrroles by the alkylation-cyclization sequence.

UR - https://www.mendeley.com/catalogue/ee9c3f3f-b597-376d-aa58-e4ff2d1f8d21/

U2 - 10.1021/acs.joc.4c00264

DO - 10.1021/acs.joc.4c00264

M3 - Article

VL - 89

SP - 6281

EP - 6291

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 9

ER -

ID: 119944543