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Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine. / Таишев, Артур Эдуардович; Галенко, Екатерина Евгениевна; Новиков, Михаил Сергеевич; Хлебников, Александр Феодосиевич.

в: Russian Journal of General Chemistry, Том 93, № 5, 01.05.2023, стр. 1246-1260.

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

Harvard

Таишев, АЭ, Галенко, ЕЕ, Новиков, МС & Хлебников, АФ 2023, 'Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine.', Russian Journal of General Chemistry, Том. 93, № 5, стр. 1246-1260. https://doi.org/10.1134/S1070363223050250

APA

Таишев, А. Э., Галенко, Е. Е., Новиков, М. С., & Хлебников, А. Ф. (2023). Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine. Russian Journal of General Chemistry, 93(5), 1246-1260. https://doi.org/10.1134/S1070363223050250

Vancouver

Таишев АЭ, Галенко ЕЕ, Новиков МС, Хлебников АФ. Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine. Russian Journal of General Chemistry. 2023 Май 1;93(5):1246-1260. https://doi.org/10.1134/S1070363223050250

Author

Таишев, Артур Эдуардович ; Галенко, Екатерина Евгениевна ; Новиков, Михаил Сергеевич ; Хлебников, Александр Феодосиевич. / Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine. в: Russian Journal of General Chemistry. 2023 ; Том 93, № 5. стр. 1246-1260.

BibTeX

@article{e63e89426c414aec8279405024abaa65,
title = "Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine.",
abstract = "Abstract: The synthesis of substituted isoxazole–oxazole hybrids by the noncatalytic reaction of methyl 2-diazo-2-(alkyl/aryl/hetarylisoxazol-5-yl)acetates with alkyl and aryl cyanides has been reported. According to DFT calculations, the reaction proceeds through the intermediate formation of a nitrile ylide and its subsequent cyclization at the carbonyl oxygen. The reaction of acrylonitrile with methyl 2-diazo-2-(isoxazol-5-yl)acetate proceeds quite differently and leads to a mixture of the cis and trans isomers of cyclopropanes, which, according to DFT calculations, are formed by the cycloaddition of a diazo-derived carbene to the C=C bond of acrylonitrile. The hetero-Diels–Alder reaction of the 5-alkoxyoxazole moiety of isoxazole–oxazole hybrids makes it possible to obtain isoxazole–pyridine hybrids, albeit in low yield.",
keywords = "diazo compounds, heterocyclic hybrids, isoxazoles, oxazoles, pyridines",
author = "Таишев, {Артур Эдуардович} and Галенко, {Екатерина Евгениевна} and Новиков, {Михаил Сергеевич} and Хлебников, {Александр Феодосиевич}",
year = "2023",
month = may,
day = "1",
doi = "10.1134/S1070363223050250",
language = "English",
volume = "93",
pages = "1246--1260",
journal = "Russian Journal of General Chemistry",
issn = "1070-3632",
publisher = "МАИК {"}Наука/Интерпериодика{"}",
number = "5",

}

RIS

TY - JOUR

T1 - Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine.

AU - Таишев, Артур Эдуардович

AU - Галенко, Екатерина Евгениевна

AU - Новиков, Михаил Сергеевич

AU - Хлебников, Александр Феодосиевич

PY - 2023/5/1

Y1 - 2023/5/1

N2 - Abstract: The synthesis of substituted isoxazole–oxazole hybrids by the noncatalytic reaction of methyl 2-diazo-2-(alkyl/aryl/hetarylisoxazol-5-yl)acetates with alkyl and aryl cyanides has been reported. According to DFT calculations, the reaction proceeds through the intermediate formation of a nitrile ylide and its subsequent cyclization at the carbonyl oxygen. The reaction of acrylonitrile with methyl 2-diazo-2-(isoxazol-5-yl)acetate proceeds quite differently and leads to a mixture of the cis and trans isomers of cyclopropanes, which, according to DFT calculations, are formed by the cycloaddition of a diazo-derived carbene to the C=C bond of acrylonitrile. The hetero-Diels–Alder reaction of the 5-alkoxyoxazole moiety of isoxazole–oxazole hybrids makes it possible to obtain isoxazole–pyridine hybrids, albeit in low yield.

AB - Abstract: The synthesis of substituted isoxazole–oxazole hybrids by the noncatalytic reaction of methyl 2-diazo-2-(alkyl/aryl/hetarylisoxazol-5-yl)acetates with alkyl and aryl cyanides has been reported. According to DFT calculations, the reaction proceeds through the intermediate formation of a nitrile ylide and its subsequent cyclization at the carbonyl oxygen. The reaction of acrylonitrile with methyl 2-diazo-2-(isoxazol-5-yl)acetate proceeds quite differently and leads to a mixture of the cis and trans isomers of cyclopropanes, which, according to DFT calculations, are formed by the cycloaddition of a diazo-derived carbene to the C=C bond of acrylonitrile. The hetero-Diels–Alder reaction of the 5-alkoxyoxazole moiety of isoxazole–oxazole hybrids makes it possible to obtain isoxazole–pyridine hybrids, albeit in low yield.

KW - diazo compounds

KW - heterocyclic hybrids

KW - isoxazoles

KW - oxazoles

KW - pyridines

UR - https://www.mendeley.com/catalogue/22082b77-f25e-3162-9411-9aee3712161d/

U2 - 10.1134/S1070363223050250

DO - 10.1134/S1070363223050250

M3 - Article

VL - 93

SP - 1246

EP - 1260

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 5

ER -

ID: 107200342