Gold-Catalyzed 1,3-Thiazine Formation and Uncommon Tautomer Isolation

This work represents the first example of a gold-catalyzed formation of 1,3-thiazine/1,3-thiazinane by means of a catalytic approach and further uncommon isolation of the two tautomers. The developed protocol gives rise to a broad scope of 1,3-thiazine derivatives with excellent yields in short reac...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-08, Vol.87 (16), p.10747-10754
Main Authors: Canudo-Barreras, Guillermo, Salvador, Daniel, Herrera, Raquel P., Gimeno, M. Concepción
Format: Article
Language:English
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Summary:This work represents the first example of a gold-catalyzed formation of 1,3-thiazine/1,3-thiazinane by means of a catalytic approach and further uncommon isolation of the two tautomers. The developed protocol gives rise to a broad scope of 1,3-thiazine derivatives with excellent yields in short reaction times. Interestingly, different isomers could be obtained depending on the state of the compound, and in the crystal state the 1,3-thiazinane isomer is obtained, while in solution the 1,3-thiazine is the unique isomer. This work represents an interesting approach for the synthesis of potential biologically relevant molecules and a crucial precedent in tautomerism isolation and characterization.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00947