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Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones. / Панькова, Алена Сергеевна; Голубев, Павел Романович; Молин, Илья Александрович; Ростовский, Николай Витальевич.

In: European Journal of Organic Chemistry, Vol. 26, No. 34, e202300573, 17.08.2023.

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

Harvard

Панькова, АС, Голубев, ПР, Молин, ИА & Ростовский, НВ 2023, 'Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones', European Journal of Organic Chemistry, vol. 26, no. 34, e202300573. https://doi.org/10.1002/ejoc.202300573

APA

Панькова, А. С., Голубев, П. Р., Молин, И. А., & Ростовский, Н. В. (2023). Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones. European Journal of Organic Chemistry, 26(34), [e202300573]. https://doi.org/10.1002/ejoc.202300573

Vancouver

Панькова АС, Голубев ПР, Молин ИА, Ростовский НВ. Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones. European Journal of Organic Chemistry. 2023 Aug 17;26(34). e202300573. https://doi.org/10.1002/ejoc.202300573

Author

Панькова, Алена Сергеевна ; Голубев, Павел Романович ; Молин, Илья Александрович ; Ростовский, Николай Витальевич. / Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones. In: European Journal of Organic Chemistry. 2023 ; Vol. 26, No. 34.

BibTeX

@article{3ae498af816a42d1b5eaede35c6f4bf8,
title = "Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones",
abstract = "Exclusive formation of 5-aryl-2-trimethylsilyl-4H-pyran-4-ones is accomplished by a regioselective cyclization of 2-aryl-1-ethoxy(hydroxy)-5-(trimethylsilyl)pent-1-en-4-yn-3-ones. This cyclization occurs in a 6-endo-dig mode through addition to the β-atom of the TMS substituted triple bond. The reaction was found to be general for a range of ethoxyenynones upon heating in glacial acetic acid and for analogous hydroxyenynones in diphenyl ether. Plausible mechanistic explanation and possible post-modifications of resulting pyranones are offered.",
keywords = "cyclization, enynone, pyran-4-one, synthetic methods",
author = "Панькова, {Алена Сергеевна} and Голубев, {Павел Романович} and Молин, {Илья Александрович} and Ростовский, {Николай Витальевич}",
year = "2023",
month = aug,
day = "17",
doi = "10.1002/ejoc.202300573",
language = "English",
volume = "26",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "34",

}

RIS

TY - JOUR

T1 - Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones

AU - Панькова, Алена Сергеевна

AU - Голубев, Павел Романович

AU - Молин, Илья Александрович

AU - Ростовский, Николай Витальевич

PY - 2023/8/17

Y1 - 2023/8/17

N2 - Exclusive formation of 5-aryl-2-trimethylsilyl-4H-pyran-4-ones is accomplished by a regioselective cyclization of 2-aryl-1-ethoxy(hydroxy)-5-(trimethylsilyl)pent-1-en-4-yn-3-ones. This cyclization occurs in a 6-endo-dig mode through addition to the β-atom of the TMS substituted triple bond. The reaction was found to be general for a range of ethoxyenynones upon heating in glacial acetic acid and for analogous hydroxyenynones in diphenyl ether. Plausible mechanistic explanation and possible post-modifications of resulting pyranones are offered.

AB - Exclusive formation of 5-aryl-2-trimethylsilyl-4H-pyran-4-ones is accomplished by a regioselective cyclization of 2-aryl-1-ethoxy(hydroxy)-5-(trimethylsilyl)pent-1-en-4-yn-3-ones. This cyclization occurs in a 6-endo-dig mode through addition to the β-atom of the TMS substituted triple bond. The reaction was found to be general for a range of ethoxyenynones upon heating in glacial acetic acid and for analogous hydroxyenynones in diphenyl ether. Plausible mechanistic explanation and possible post-modifications of resulting pyranones are offered.

KW - cyclization

KW - enynone

KW - pyran-4-one

KW - synthetic methods

UR - https://www.mendeley.com/catalogue/0e623622-b785-3940-92f4-0eeeabfc3f0e/

U2 - 10.1002/ejoc.202300573

DO - 10.1002/ejoc.202300573

M3 - Article

VL - 26

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 34

M1 - e202300573

ER -

ID: 110605535