Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
J Org Chem. 2023 Feb 17;88(4):2561-2569. doi: 10.1021/acs.joc.2c02463. Epub 2023 Jan 31.
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 -quinones and thiols were developed. The mild conditions proved amenable to a wide scope of both thiol and -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.
在此，我们受黑色素生物合成（真黑素生成）的启发，报告了一种合成 1,4-苯并噻嗪的仿生方法。在这种情况下，开发了 - 醌和硫醇之间区域选择性偶联反应的一般条件。温和的条件适用于广泛的硫醇和 - 醌偶联物，同时抑制氧化还原交换。该方法的实用性通过生物模拟的氧化环化反应合成 1,4-苯并噻嗪得到了证明。
