Standard

Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization. / Usachev, Sergey A.; Fedin, Vladislav V.; Obydennov, Dmitrii et al.
In: Tetrahedron Letters, Vol. 128, 154682, 01.09.2023.

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

Harvard

Usachev, SA, Fedin, VV, Obydennov, D & Sosnovskikh, VY 2023, 'Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization', Tetrahedron Letters, vol. 128, 154682. https://doi.org/10.1016/j.tetlet.2023.154682

APA

Usachev, S. A., Fedin, V. V., Obydennov, D., & Sosnovskikh, V. Y. (2023). Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization. Tetrahedron Letters, 128, [154682]. https://doi.org/10.1016/j.tetlet.2023.154682

Vancouver

Usachev SA, Fedin VV, Obydennov D, Sosnovskikh VY. Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization. Tetrahedron Letters. 2023 Sept 1;128:154682. doi: 10.1016/j.tetlet.2023.154682

Author

Usachev, Sergey A. ; Fedin, Vladislav V. ; Obydennov, Dmitrii et al. / Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization. In: Tetrahedron Letters. 2023 ; Vol. 128.

BibTeX

@article{3abcffb93c8e4867be7443b989bb481b,
title = "Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization",
abstract = "The tandem acylation-heterocyclization of ketene dithioacetals was performed via soft enolization in MgBr2·OEt2/NEt3 system. A series of 3,6-substituted 2-methylthio-4-pyrones were obtained with a wide functional group tolerance. The reaction showed a good scalability, and the isolation of the products was performed by crystallization without the use of chromatography. Some transformations of the obtained 2-methylthio-4-pyrones, including substitution of the SMe group with N-nucleophiles, have been demonstrated for the preparation of functionalized 4-pyrones as analogs of several bioactive molecules.",
author = "Usachev, {Sergey A.} and Fedin, {Vladislav V.} and Dmitrii Obydennov and Sosnovskikh, {Vyacheslav Y.}",
note = "This work was financially supported by the Russian Science Foundation (Grant 22-73-10236). Authors would like to thank Marina Mikheeva for her help in the work.",
year = "2023",
month = sep,
day = "1",
doi = "10.1016/j.tetlet.2023.154682",
language = "English",
volume = "128",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of 3,6-substituted 2-methylthio-4-pyrones by acylation of ketene dithioacetals via soft enolization

AU - Usachev, Sergey A.

AU - Fedin, Vladislav V.

AU - Obydennov, Dmitrii

AU - Sosnovskikh, Vyacheslav Y.

N1 - This work was financially supported by the Russian Science Foundation (Grant 22-73-10236). Authors would like to thank Marina Mikheeva for her help in the work.

PY - 2023/9/1

Y1 - 2023/9/1

N2 - The tandem acylation-heterocyclization of ketene dithioacetals was performed via soft enolization in MgBr2·OEt2/NEt3 system. A series of 3,6-substituted 2-methylthio-4-pyrones were obtained with a wide functional group tolerance. The reaction showed a good scalability, and the isolation of the products was performed by crystallization without the use of chromatography. Some transformations of the obtained 2-methylthio-4-pyrones, including substitution of the SMe group with N-nucleophiles, have been demonstrated for the preparation of functionalized 4-pyrones as analogs of several bioactive molecules.

AB - The tandem acylation-heterocyclization of ketene dithioacetals was performed via soft enolization in MgBr2·OEt2/NEt3 system. A series of 3,6-substituted 2-methylthio-4-pyrones were obtained with a wide functional group tolerance. The reaction showed a good scalability, and the isolation of the products was performed by crystallization without the use of chromatography. Some transformations of the obtained 2-methylthio-4-pyrones, including substitution of the SMe group with N-nucleophiles, have been demonstrated for the preparation of functionalized 4-pyrones as analogs of several bioactive molecules.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85167962393

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001063414000001

U2 - 10.1016/j.tetlet.2023.154682

DO - 10.1016/j.tetlet.2023.154682

M3 - Article

VL - 128

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 154682

ER -

ID: 43605358