Standard

Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways. / Васильченко, Дмитрий Сергеевич; Агафонова, Анастасия Викторовна; Хлебников, Александр Феодосиевич; Ростовский, Николай Витальевич; Новиков, Михаил Сергеевич.

In: Organic Chemistry Frontiers, 15.10.2025.

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

Harvard

Васильченко, ДС, Агафонова, АВ, Хлебников, АФ, Ростовский, НВ & Новиков, МС 2025, 'Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways', Organic Chemistry Frontiers. https://doi.org/10.1039/D5QO01233C

APA

Васильченко, Д. С., Агафонова, А. В., Хлебников, А. Ф., Ростовский, Н. В., & Новиков, М. С. (2025). Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways. Organic Chemistry Frontiers. https://doi.org/10.1039/D5QO01233C

Vancouver

Васильченко ДС, Агафонова АВ, Хлебников АФ, Ростовский НВ, Новиков МС. Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways. Organic Chemistry Frontiers. 2025 Oct 15. https://doi.org/10.1039/D5QO01233C

Author

Васильченко, Дмитрий Сергеевич ; Агафонова, Анастасия Викторовна ; Хлебников, Александр Феодосиевич ; Ростовский, Николай Витальевич ; Новиков, Михаил Сергеевич. / Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways. In: Organic Chemistry Frontiers. 2025.

BibTeX

@article{cf63251337f94cfa829fa86ca257ead5,
title = "Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways",
abstract = "S-Azirinyl xanthates were synthesized as novel 2H-azirine derivatives exhibiting dual reactivity toward free radicals. Carbon-, tin-, and silicon-centered radicals initiate a desulfurization/ring expansion cascade of these compounds to form thiazoles in fair to good yields. Radicals can react with azirinyl xanthates either at the nitrogen (stannyl radicals) or sulfur (alkyl and silyl radicals), transforming them into the thiazoles through the intermediate formation of either aziridinyl or thiaazabicyclopentyl radicals, respectively. Both transformations do not involve the degenerative radical transfer and are unprecedented for the radical chemistry of xanthates.",
author = "Васильченко, {Дмитрий Сергеевич} and Агафонова, {Анастасия Викторовна} and Хлебников, {Александр Феодосиевич} and Ростовский, {Николай Витальевич} and Новиков, {Михаил Сергеевич}",
year = "2025",
month = oct,
day = "15",
doi = "10.1039/D5QO01233C",
language = "English",
journal = "Organic Chemistry Frontiers",
issn = "2052-4110",
publisher = "Royal Society of Chemistry",

}

RIS

TY - JOUR

T1 - Synthesis of thiazoles by desulfurative cyclization/ring expansion cascade reaction of S-azirinyl xanthates: two mechanistically distinct radical pathways

AU - Васильченко, Дмитрий Сергеевич

AU - Агафонова, Анастасия Викторовна

AU - Хлебников, Александр Феодосиевич

AU - Ростовский, Николай Витальевич

AU - Новиков, Михаил Сергеевич

PY - 2025/10/15

Y1 - 2025/10/15

N2 - S-Azirinyl xanthates were synthesized as novel 2H-azirine derivatives exhibiting dual reactivity toward free radicals. Carbon-, tin-, and silicon-centered radicals initiate a desulfurization/ring expansion cascade of these compounds to form thiazoles in fair to good yields. Radicals can react with azirinyl xanthates either at the nitrogen (stannyl radicals) or sulfur (alkyl and silyl radicals), transforming them into the thiazoles through the intermediate formation of either aziridinyl or thiaazabicyclopentyl radicals, respectively. Both transformations do not involve the degenerative radical transfer and are unprecedented for the radical chemistry of xanthates.

AB - S-Azirinyl xanthates were synthesized as novel 2H-azirine derivatives exhibiting dual reactivity toward free radicals. Carbon-, tin-, and silicon-centered radicals initiate a desulfurization/ring expansion cascade of these compounds to form thiazoles in fair to good yields. Radicals can react with azirinyl xanthates either at the nitrogen (stannyl radicals) or sulfur (alkyl and silyl radicals), transforming them into the thiazoles through the intermediate formation of either aziridinyl or thiaazabicyclopentyl radicals, respectively. Both transformations do not involve the degenerative radical transfer and are unprecedented for the radical chemistry of xanthates.

U2 - 10.1039/D5QO01233C

DO - 10.1039/D5QO01233C

M3 - Article

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

ER -

ID: 143421224