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 Full article

Journal

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

Output data

Year: 2026, Volume: 24, Number: 1, Pages: 136-141 Pages count : 6 DOI: 10.1039/d5ob01543j

Authors

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

Affiliations

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

Funding (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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