A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3<i>H</i>)-one

A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3<i>H</i>)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C-H bond thiolation, and nucleophilic cascade cyclization to build the (C-S/C-N) bonds to construct the C-O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.

Authors

Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-07
DOI
https://doi.org/10.1021/acs.joc.4c01800
Citations
3
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.75

Funders

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article

A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

Ganpeng Li, Yonghui He, Yuefa Gong, Yuqi Shi et al.
3 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.75
article

A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

Ganpeng Li, Yonghui He, Yuefa Gong, Yuqi Shi, Qinyu Zhao, Xiaojing Zhao, Mingxu Wang
article en
3 citations

Abstract

A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3<i>H</i>)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C-H bond thiolation, and nucleophilic cascade cyclization to build the (C-S/C-N) bonds to construct the C-O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.

The Journal of Organic ChemistryVol. 89(23)
Applied Basic Research Key Project of Yunnan
Clean water and sanitation
Openalex Percentile: Top 31%
Sulfur-Based Synthesis Techniques
0.75
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A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3<i>H</i>)-one — Ganpeng Li, Yonghui He, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS