Synthesis of thiazoles from vinyl azides and xanthates under the action of an Mn( iii )-oxidant

Synthesis of thiazoles from vinyl azides and xanthates under the action of an Mn( iii )-oxidant Научная публикация

Журнал

Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Вых. Данные

Год: 2026, Том: 24, Номер: 1, Страницы: 136-141 Страниц : 6 DOI: 10.1039/d5ob01543j

Авторы

Zaikina Lada A. ^1,2 , Doronin Mikhail M. ² , Segida Oleg O. ² , Mulina Olga M. ² , Krylov Igor B. ^1,2 , He Liang-Nian ³ , Terent'ev Alexander O. ^1,2

Организации

1	Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation
2	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, Moscow, 119991, Russian Federation
3	State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, P. R. China

Информация о финансировании (1)

Reaction of xanthates and vinyl azides under the action of Mn(OAc)3 results in the formation of alkoxy thiazoles. In this transformation, potassium xanthate undergoes Mn-mediated oxidation, generating the corresponding xanthyl radical. The latter interacts with the double bond of the vinyl azide, and after N2 elimination, a β-xanthylated iminyl radical is formed. The quenching of the iminyl radical by an Mn(II)-ion with subsequent cyclization into a 5-membered ring, an unexpected elimination of a sulfur-containing fragment and aromatization lead to thiazoles. It is important to mention that cyclization with the formation of a 6-membered ring is not observed in the disclosed process. The obtained thiazoles demonstrate antifungal activity surpassing that of commercially available fungicides.

Zaikina L.A. , Doronin M.M. , Segida O.O. , Mulina O.M. , Krylov I.B. , He L-N. , Terent'ev A.O.
Synthesis of thiazoles from vinyl azides and xanthates under the action of an Mn( iii )-oxidant
Organic and Biomolecular Chemistry. 2026. V.24. N1. P.136-141. DOI: 10.1039/d5ob01543j WOS Scopus OpenAlex

Web of science:	WOS:001628026800001
Scopus:	2-s2.0-105023301580
OpenAlex:	W4416319121

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