Synthesis of Benzothiazolopyrimidine Diastereomers Through a Copper‐Catalyzed Azide–Alkyne Cycloaddition/Ring‐Cleavage/[4 + 2] Cycloaddition Sequence

Copper‐catalyzed reactions of 2‐benzothiazolimines, terminal ynones, and sulfonyl azides afforded benzothiazolopyrimidine diastereomers. The transformation involved a tandem CuAAC/ring‐cleavage/[4 + 2] cycloaddition procedure with one‐pot synthesis under mild conditions. The benzothiazolopyrimidine diastereomers could be isolated, and their structure is confirmed by X‐ray single‐crystal diffraction.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-12-05
DOI
https://doi.org/10.1002/ejoc.202500714
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Synthesis of Benzothiazolopyrimidine Diastereomers Through a Copper‐Catalyzed Azide–Alkyne Cycloaddition/Ring‐Cleavage/[4 + 2] Cycloaddition Sequence

Ao Qi, Qiaoli Luo, Weiguang Yang, Xiaoyan Su et al.
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Synthesis of Benzothiazolopyrimidine Diastereomers Through a Copper‐Catalyzed Azide–Alkyne Cycloaddition/Ring‐Cleavage/[4 + 2] Cycloaddition Sequence

Ao Qi, Qiaoli Luo, Weiguang Yang, Xiaoyan Su, Hua Ye, Hang Li, Liu Yang, Jing Shen, Zixin Huang
article en

Abstract

Copper‐catalyzed reactions of 2‐benzothiazolimines, terminal ynones, and sulfonyl azides afforded benzothiazolopyrimidine diastereomers. The transformation involved a tandem CuAAC/ring‐cleavage/[4 + 2] cycloaddition procedure with one‐pot synthesis under mild conditions. The benzothiazolopyrimidine diastereomers could be isolated, and their structure is confirmed by X‐ray single‐crystal diffraction.

European Journal of Organic ChemistryVol. 29(3)
Lingnan Normal University (CN), Guangdong Medical College (CN), Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (CN)
Openalex Percentile: Top 71%
Catalytic C–H Functionalization Methods
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Synthesis of Benzothiazolopyrimidine Diastereomers Through a Copper‐Catalyzed Azide–Alkyne Cycloaddition/Ring‐Cleavage/[4 + 2] Cycloaddition Sequence — Ao Qi, Qiaoli Luo, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS