Standard

Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines. / Щербаков, Николай Викторович; Дарьин, Дмитрий Викторович; Дубовцев, Алексей Юрьевич; Зверева, Валерия Владиславовна; Кукушкин, Вадим Юрьевич; Новиков, Александр Сергеевич.

In: Organic and Biomolecular Chemistry, Vol. 19, No. 20, 28.05.2021, p. 4577-4584.

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

Harvard

Щербаков, НВ, Дарьин, ДВ, Дубовцев, АЮ, Зверева, ВВ, Кукушкин, ВЮ & Новиков, АС 2021, 'Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines', Organic and Biomolecular Chemistry, vol. 19, no. 20, pp. 4577-4584. https://doi.org/10.1039/D1OB00513H

APA

Щербаков, Н. В., Дарьин, Д. В., Дубовцев, А. Ю., Зверева, В. В., Кукушкин, В. Ю., & Новиков, А. С. (2021). Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines. Organic and Biomolecular Chemistry, 19(20), 4577-4584. https://doi.org/10.1039/D1OB00513H

Vancouver

Щербаков НВ, Дарьин ДВ, Дубовцев АЮ, Зверева ВВ, Кукушкин ВЮ, Новиков АС. Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines. Organic and Biomolecular Chemistry. 2021 May 28;19(20):4577-4584. https://doi.org/10.1039/D1OB00513H

Author

Щербаков, Николай Викторович ; Дарьин, Дмитрий Викторович ; Дубовцев, Алексей Юрьевич ; Зверева, Валерия Владиславовна ; Кукушкин, Вадим Юрьевич ; Новиков, Александр Сергеевич. / Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines. In: Organic and Biomolecular Chemistry. 2021 ; Vol. 19, No. 20. pp. 4577-4584.

BibTeX

@article{449e63c35b0d4e0ab0feec44c2a5c655,
title = "Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines",
abstract = "Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed density functional theory calculations verified a particular role of H+, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition.",
author = "Щербаков, {Николай Викторович} and Дарьин, {Дмитрий Викторович} and Дубовцев, {Алексей Юрьевич} and Зверева, {Валерия Владиславовна} and Кукушкин, {Вадим Юрьевич} and Новиков, {Александр Сергеевич}",
note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",
year = "2021",
month = may,
day = "28",
doi = "10.1039/D1OB00513H",
language = "English",
volume = "19",
pages = "4577--4584",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "20",

}

RIS

TY - JOUR

T1 - Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines

AU - Щербаков, Николай Викторович

AU - Дарьин, Дмитрий Викторович

AU - Дубовцев, Алексей Юрьевич

AU - Зверева, Валерия Владиславовна

AU - Кукушкин, Вадим Юрьевич

AU - Новиков, Александр Сергеевич

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

PY - 2021/5/28

Y1 - 2021/5/28

N2 - Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed density functional theory calculations verified a particular role of H+, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition.

AB - Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed density functional theory calculations verified a particular role of H+, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition.

UR - http://www.scopus.com/inward/record.url?scp=85106641521&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/1f97d42a-0541-30d4-b8ce-18bdefc94586/

U2 - 10.1039/D1OB00513H

DO - 10.1039/D1OB00513H

M3 - Article

VL - 19

SP - 4577

EP - 4584

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 20

ER -

ID: 85051614