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Cascade transformation of 2-(diazoacetyl)-2H-azirines to 2-aroyl-3-hydroxy-1H-pyrroles via condensation with aromatic aldehydes. / Занахов, Тимур Олегович; Галенко, Екатерина Евгениевна; Новиков, Михаил Сергеевич; Хлебников, Александр Феодосиевич.

в: Beilstein Journal of Organic Chemistry, Том 22, 09.06.2026, стр. 897–904.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

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@article{022e4316e49f455bbb1b07b1bb338443,
title = "Cascade transformation of 2-(diazoacetyl)-2H-azirines to 2-aroyl-3-hydroxy-1H-pyrroles via condensation with aromatic aldehydes",
abstract = "The Cs2CO3 -induced condensation of 2-(diazoacetyl)-2H-azirines with aromatic aldehydes does not result in the formation of anazirinyl-substituted β-hydroxy-α-diazocarbonyl compound, but is accompanied by a tandem intramolecular cyclization involving the hydroxy group and the C=N bond of the azirine to form a bicyclic intermediate, a 4-diazo-2-oxa-7-azabicyclo[4.1.0]heptan-5-one derivative. The acid-catalyzed transformation of which leads to 2-aroyl-3-hydroxy-1H-pyrroles.",
author = "Занахов, {Тимур Олегович} and Галенко, {Екатерина Евгениевна} and Новиков, {Михаил Сергеевич} and Хлебников, {Александр Феодосиевич}",
year = "2026",
month = jun,
day = "9",
doi = "10.3762/bjoc.22.70",
language = "English",
volume = "22",
pages = "897–904",
journal = "Beilstein Journal of Organic Chemistry",
issn = "2195-951X",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Cascade transformation of 2-(diazoacetyl)-2H-azirines to 2-aroyl-3-hydroxy-1H-pyrroles via condensation with aromatic aldehydes

AU - Занахов, Тимур Олегович

AU - Галенко, Екатерина Евгениевна

AU - Новиков, Михаил Сергеевич

AU - Хлебников, Александр Феодосиевич

PY - 2026/6/9

Y1 - 2026/6/9

N2 - The Cs2CO3 -induced condensation of 2-(diazoacetyl)-2H-azirines with aromatic aldehydes does not result in the formation of anazirinyl-substituted β-hydroxy-α-diazocarbonyl compound, but is accompanied by a tandem intramolecular cyclization involving the hydroxy group and the C=N bond of the azirine to form a bicyclic intermediate, a 4-diazo-2-oxa-7-azabicyclo[4.1.0]heptan-5-one derivative. The acid-catalyzed transformation of which leads to 2-aroyl-3-hydroxy-1H-pyrroles.

AB - The Cs2CO3 -induced condensation of 2-(diazoacetyl)-2H-azirines with aromatic aldehydes does not result in the formation of anazirinyl-substituted β-hydroxy-α-diazocarbonyl compound, but is accompanied by a tandem intramolecular cyclization involving the hydroxy group and the C=N bond of the azirine to form a bicyclic intermediate, a 4-diazo-2-oxa-7-azabicyclo[4.1.0]heptan-5-one derivative. The acid-catalyzed transformation of which leads to 2-aroyl-3-hydroxy-1H-pyrroles.

U2 - 10.3762/bjoc.22.70

DO - 10.3762/bjoc.22.70

M3 - Article

VL - 22

SP - 897

EP - 904

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 2195-951X

ER -

ID: 155510908