Standard

Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines. / Агафонова, Анастасия Викторовна; Голубев, Артём Алексеевич; Сметанин, Илья Алексеевич; Хлебников, Александр Феодосиевич; Спиридонова, Дарья Валерьевна; Новиков, Михаил Сергеевич.

в: Organic Letters, Том 25, № 39, 06.10.2023, стр. 7165−7169.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Агафонова, АВ, Голубев, АА, Сметанин, ИА, Хлебников, АФ, Спиридонова, ДВ & Новиков, МС 2023, 'Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines', Organic Letters, Том. 25, № 39, стр. 7165−7169. https://doi.org/10.1021/acs.orglett.3c02696

APA

Агафонова, А. В., Голубев, А. А., Сметанин, И. А., Хлебников, А. Ф., Спиридонова, Д. В., & Новиков, М. С. (2023). Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines. Organic Letters, 25(39), 7165−7169. https://doi.org/10.1021/acs.orglett.3c02696

Vancouver

Агафонова АВ, Голубев АА, Сметанин ИА, Хлебников АФ, Спиридонова ДВ, Новиков МС. Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines. Organic Letters. 2023 Окт. 6;25(39):7165−7169. https://doi.org/10.1021/acs.orglett.3c02696

Author

Агафонова, Анастасия Викторовна ; Голубев, Артём Алексеевич ; Сметанин, Илья Алексеевич ; Хлебников, Александр Феодосиевич ; Спиридонова, Дарья Валерьевна ; Новиков, Михаил Сергеевич. / Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines. в: Organic Letters. 2023 ; Том 25, № 39. стр. 7165−7169.

BibTeX

@article{713a9e54748b46369f3ac806c5eebd31,
title = "Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines",
abstract = "The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion products of pyrazolo[1,5-a]pyridine or imidazo[1,5-a]pyridine series, respectively. Mild catalytic reaction conditions for the formation of pyrazolopyridines make it possible to obtain them directly from 4-bromoisoxazoles by a one-pot, three-stage procedure without isolating the intermediate 2-bromoazirines and 2-(2-pyridyl)azirines.",
author = "Агафонова, {Анастасия Викторовна} and Голубев, {Артём Алексеевич} and Сметанин, {Илья Алексеевич} and Хлебников, {Александр Феодосиевич} and Спиридонова, {Дарья Валерьевна} and Новиков, {Михаил Сергеевич}",
year = "2023",
month = oct,
day = "6",
doi = "10.1021/acs.orglett.3c02696",
language = "English",
volume = "25",
pages = "7165−7169",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "39",

}

RIS

TY - JOUR

T1 - Divergent Synthesis of Pyrazolo[1,5‑a]pyridines and Imidazo[1,5‑a]pyridines via Reagent-Controlled Cleavage of the C−N or C−C Azirine Bond in 2‑Pyridylazirines

AU - Агафонова, Анастасия Викторовна

AU - Голубев, Артём Алексеевич

AU - Сметанин, Илья Алексеевич

AU - Хлебников, Александр Феодосиевич

AU - Спиридонова, Дарья Валерьевна

AU - Новиков, Михаил Сергеевич

PY - 2023/10/6

Y1 - 2023/10/6

N2 - The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion products of pyrazolo[1,5-a]pyridine or imidazo[1,5-a]pyridine series, respectively. Mild catalytic reaction conditions for the formation of pyrazolopyridines make it possible to obtain them directly from 4-bromoisoxazoles by a one-pot, three-stage procedure without isolating the intermediate 2-bromoazirines and 2-(2-pyridyl)azirines.

AB - The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion products of pyrazolo[1,5-a]pyridine or imidazo[1,5-a]pyridine series, respectively. Mild catalytic reaction conditions for the formation of pyrazolopyridines make it possible to obtain them directly from 4-bromoisoxazoles by a one-pot, three-stage procedure without isolating the intermediate 2-bromoazirines and 2-(2-pyridyl)azirines.

UR - https://www.mendeley.com/catalogue/1b5ff1b8-9b65-3aac-922d-9499d0915121/

U2 - 10.1021/acs.orglett.3c02696

DO - 10.1021/acs.orglett.3c02696

M3 - Article

VL - 25

SP - 7165−7169

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 39

ER -

ID: 113635673