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

Alkyl and silyl radicals react with S -azirinyl xanthates at the nitrogen atom, while stannyl radicals – at the sulfur atom, leading in two different ways to the formation of azirine ring expansion products, 2-alkoxythiazole-5-carboxylic esters.

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Publication Details

Journal
Organic Chemistry Frontiers
Published
2025-10-15
DOI
https://doi.org/10.1039/d5qo01233c
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

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

Alexander F. Khlebnikov, Николай В. Ростовский, Anastasiya V. Agafonova, Dmitrii Sergeevich Vasilchenko et al.
Organic Chemistry Frontiers
Synthesis and Catalytic Reactions
article

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

Alexander F. Khlebnikov, Николай В. Ростовский, Anastasiya V. Agafonova, Dmitrii Sergeevich Vasilchenko, Михаил С. Новиков
article en

Abstract

Alkyl and silyl radicals react with S -azirinyl xanthates at the nitrogen atom, while stannyl radicals – at the sulfur atom, leading in two different ways to the formation of azirine ring expansion products, 2-alkoxythiazole-5-carboxylic esters.

Organic Chemistry FrontiersVol. 13(1)
St Petersburg University (RU)
Openalex Percentile: Top 78%
Synthesis and Catalytic Reactions
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