A Bioinspired Synthesis of 1,4-Benzothiazines by Selective Addition of Sulfur Nucleophiles to ortho-Quinones

被引：5

作者：

Halloran, Matthew W. ^{[1
]}

Li, Elizabeth ^{[1
]}

Esguerra, Kenneth Virgel N. ^{[1
]}

Lumb, Jean-Philip ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 04期

基金：

加拿大自然科学与工程研究理事会;

关键词：

DERIVATIVES; OXIDATION; CYSTEINE; BENZOTHIAZINES; REACTIVITY; CHEMISTRY; PHENOLS; DOPA; RED;

D O I：

10.1021/acs.joc.2c02463

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2561 / 2569

页数：9

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