A Bioinspired Synthesis of 1,4-Benzothiazines by Selective Addition of Sulfur Nucleophiles to ortho-Quinones.
J Org Chem
; 88(4): 2561-2569, 2023 Feb 17.
Article
em En
| MEDLINE
| ID: mdl-36719706
ABSTRACT
Herein, we report a bioinspired approach to the synthesis of 1,4-benzothiazines by drawing inspiration from the biosynthesis of pheomelanin pigments (pheomelanogenesis). In this context, general conditions for the regioselective coupling reaction between ortho-quinones and thiols were developed. The mild conditions proved amenable to a wide scope of both thiol and ortho-quinone coupling partners while simultaneously suppressing redox-exchange. The utility of this methodology was demonstrated by a synthesis of 1,4-benzothiazines, following a biomimetic, oxidative cyclization.
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MEDLINE
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En
Ano de publicação:
2023
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Article