Skeleton Editingof Benzothiazoles to Spiro[benzothiazole‑<i>n</i>‑alkanes] by Carbon-to-Carbon Single-Atom Swapping

Skeleton editing can be used to precisely replace or rearrange atoms in the core ring structure of complex molecules and is often used to modify heteroaromatic compounds. However, this approach has not been used to modify thiazole rings. We report the direct construction of spiro[benzothiazole-<i>n</i>-alkanes] through skeleton editing of thiazolium salts by carbon-to-carbon single-atom swapping. Skeleton editing via carbon deletion and insertion has the advantages of high efficiency, high selectivity, simple operation, and one-step, metal-catalyst-free construction of novel spirocyclic products with novel structures.

Publication Details

Journal
Figshare
Published
2025-03-06
DOI
https://doi.org/10.1021/acs.joc.4c02876.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Skeleton Editingof Benzothiazoles to Spiro[benzothiazole‑n‑alkanes] by Carbon-to-Carbon Single-Atom Swapping

Figshare
Catalytic C–H Functionalization Methods
article

Skeleton Editingof Benzothiazoles to Spiro[benzothiazole‑n‑alkanes] by Carbon-to-Carbon Single-Atom Swapping

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Abstract

Skeleton editing can be used to precisely replace or rearrange atoms in the core ring structure of complex molecules and is often used to modify heteroaromatic compounds. However, this approach has not been used to modify thiazole rings. We report the direct construction of spiro[benzothiazole-<i>n</i>-alkanes] through skeleton editing of thiazolium salts by carbon-to-carbon single-atom swapping. Skeleton editing via carbon deletion and insertion has the advantages of high efficiency, high selectivity, simple operation, and one-step, metal-catalyst-free construction of novel spirocyclic products with novel structures.

Figshare
Openalex Percentile: Top 59%
Catalytic C–H Functionalization Methods
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Skeleton Editingof Benzothiazoles to Spiro[benzothiazole‑<i>n</i>‑alkanes] by Carbon-to-Carbon Single-Atom Swapping · Figshare (2025) | TGRS Research Map | TGRS