Gold-catalyzed 1, 3-Thiazine formation and uncommon tautomer isolation

Canudo-Barreras, G. (Universidad de Zaragoza) ; Salvador, D. ; Herrera, R. P. ; Gimeno, M. C.

Resumen: 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. © 2022 American Chemical Society. All rights reserved.

Idioma: Inglés

DOI: 10.1021/acs.joc.2c00947

Año: 2022

Publicado en: Journal of Organic Chemistry 87, 16 (2022), 10747-10754
ISSN: 0022-3263

Factor impacto JCR: 3.6 (2022)

Categ. JCR: CHEMISTRY, ORGANIC rank: 10 / 52 = 0.192 (2022) - Q1 - T1

Factor impacto CITESCORE: 6.8 - Chemistry (Q1)

Factor impacto SCIMAGO: 0.892 - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E07-20R
Financiación: info:eu-repo/grantAgreement/ES/MCIN/AEI/PID2020-117455GB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104379RB-C21-AEI-10.13039-501100011033

Tipo y forma: Article (Published version)

Área (Departamento): Área Paleontología (Dpto. Ciencias de la Tierra)