Standard

Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides. / Щербаков, Николай Викторович; Титов, Глеб Денисович; Чикунова, Елена Игоревна; Филиппов, Илья Павлович; Ростовский, Николай Витальевич; Кукушкин, Вадим Юрьевич; Дубовцев, Алексей Юрьевич.

In: Organic Chemistry Frontiers, Vol. 9, No. 19, 08.08.2022, p. 5133-5140.

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

Harvard

Щербаков, НВ, Титов, ГД, Чикунова, ЕИ, Филиппов, ИП, Ростовский, НВ, Кукушкин, ВЮ & Дубовцев, АЮ 2022, 'Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides', Organic Chemistry Frontiers, vol. 9, no. 19, pp. 5133-5140. https://doi.org/10.1039/d2qo01105k

APA

Щербаков, Н. В., Титов, Г. Д., Чикунова, Е. И., Филиппов, И. П., Ростовский, Н. В., Кукушкин, В. Ю., & Дубовцев, А. Ю. (2022). Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides. Organic Chemistry Frontiers, 9(19), 5133-5140. https://doi.org/10.1039/d2qo01105k

Vancouver

Щербаков НВ, Титов ГД, Чикунова ЕИ, Филиппов ИП, Ростовский НВ, Кукушкин ВЮ et al. Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides. Organic Chemistry Frontiers. 2022 Aug 8;9(19):5133-5140. https://doi.org/10.1039/d2qo01105k

Author

Щербаков, Николай Викторович ; Титов, Глеб Денисович ; Чикунова, Елена Игоревна ; Филиппов, Илья Павлович ; Ростовский, Николай Витальевич ; Кукушкин, Вадим Юрьевич ; Дубовцев, Алексей Юрьевич. / Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides. In: Organic Chemistry Frontiers. 2022 ; Vol. 9, No. 19. pp. 5133-5140.

BibTeX

@article{802b06aedb894bd5b19aa3b64e1a7c08,
title = "Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides",
abstract = "The developed modular approach to hard-to-reach non-aromatic 3H- and 2H-pyrroles is based on the integration of 2H-azirines and ynamides. Gold-catalyzed [3 + 2] cycloaddition of 2,2-disubstituted 2H-azirines and ynamides constitutes a high-yielding route to 5-amino-3H-pyrroles. This reaction proceeds under mild conditions (HAuCl4 5 mol%, DCM, rt) and demonstrates high functional group tolerance (more than 30 examples; yields up to 98%). As a further branch of the proposed synthetic route, we also elaborated a smooth acid-promoted 1,5-shift-based isomerization of the obtained 5-amino-3H-pyrroles to fully substituted 5-amino-2H-pyrroles (18 examples; yields up to 86%). Furthermore, if 2-substituted 2H-azirine-2-carboxylic acid is employed for the cycloaddition with ynamide, a subsequent decarboxylation leads to an aromatic 2-amino-1H-pyrrole scaffold.",
author = "Щербаков, {Николай Викторович} and Титов, {Глеб Денисович} and Чикунова, {Елена Игоревна} and Филиппов, {Илья Павлович} and Ростовский, {Николай Витальевич} and Кукушкин, {Вадим Юрьевич} and Дубовцев, {Алексей Юрьевич}",
note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",
year = "2022",
month = aug,
day = "8",
doi = "10.1039/d2qo01105k",
language = "English",
volume = "9",
pages = "5133--5140",
journal = "Organic Chemistry Frontiers",
issn = "2052-4110",
publisher = "Royal Society of Chemistry",
number = "19",

}

RIS

TY - JOUR

T1 - Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides

AU - Щербаков, Николай Викторович

AU - Титов, Глеб Денисович

AU - Чикунова, Елена Игоревна

AU - Филиппов, Илья Павлович

AU - Ростовский, Николай Витальевич

AU - Кукушкин, Вадим Юрьевич

AU - Дубовцев, Алексей Юрьевич

N1 - Publisher Copyright: © 2022 The Royal Society of Chemistry.

PY - 2022/8/8

Y1 - 2022/8/8

N2 - The developed modular approach to hard-to-reach non-aromatic 3H- and 2H-pyrroles is based on the integration of 2H-azirines and ynamides. Gold-catalyzed [3 + 2] cycloaddition of 2,2-disubstituted 2H-azirines and ynamides constitutes a high-yielding route to 5-amino-3H-pyrroles. This reaction proceeds under mild conditions (HAuCl4 5 mol%, DCM, rt) and demonstrates high functional group tolerance (more than 30 examples; yields up to 98%). As a further branch of the proposed synthetic route, we also elaborated a smooth acid-promoted 1,5-shift-based isomerization of the obtained 5-amino-3H-pyrroles to fully substituted 5-amino-2H-pyrroles (18 examples; yields up to 86%). Furthermore, if 2-substituted 2H-azirine-2-carboxylic acid is employed for the cycloaddition with ynamide, a subsequent decarboxylation leads to an aromatic 2-amino-1H-pyrrole scaffold.

AB - The developed modular approach to hard-to-reach non-aromatic 3H- and 2H-pyrroles is based on the integration of 2H-azirines and ynamides. Gold-catalyzed [3 + 2] cycloaddition of 2,2-disubstituted 2H-azirines and ynamides constitutes a high-yielding route to 5-amino-3H-pyrroles. This reaction proceeds under mild conditions (HAuCl4 5 mol%, DCM, rt) and demonstrates high functional group tolerance (more than 30 examples; yields up to 98%). As a further branch of the proposed synthetic route, we also elaborated a smooth acid-promoted 1,5-shift-based isomerization of the obtained 5-amino-3H-pyrroles to fully substituted 5-amino-2H-pyrroles (18 examples; yields up to 86%). Furthermore, if 2-substituted 2H-azirine-2-carboxylic acid is employed for the cycloaddition with ynamide, a subsequent decarboxylation leads to an aromatic 2-amino-1H-pyrrole scaffold.

UR - http://www.scopus.com/inward/record.url?scp=85136319039&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/448f65a3-0849-3fe3-bcb9-f62166c7bb9a/

U2 - 10.1039/d2qo01105k

DO - 10.1039/d2qo01105k

M3 - Article

VL - 9

SP - 5133

EP - 5140

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 19

ER -

ID: 99995976