Ma Renchao, Ding Yuxin, Chen Rener, Wang Zhiming, Wang Lei, Ma Yongmin
Institute of Advanced Studies and School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P R China.
J Org Chem. 2021 Jan 1;86(1):310-321. doi: 10.1021/acs.joc.0c02095. Epub 2020 Dec 17.
A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO or in 1,4-dioxane containing PhNO, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO/I co-catalytic system is proposed first time.
开发了一种简单实用的多米诺骨牌协议，用于在无金属条件下由I催化选择性合成2-芳酰基苯并噻唑和2-芳基苯并噻唑。反应结果完全由反应氧化剂/介质控制。当使用DMSO作为溶剂和氧化剂时，芳族甲基酮的氧化优先于与2-氨基苯硫醇的缩合。另一方面，当反应在PhNO中或在含有PhNO的1,4-二氧六环中进行时，芳族甲基酮与2-氨基苯硫醇的缩合优先形成亚胺，随后酮的甲基被氧化，得到唯一产物2-芳基苯并噻唑。首次提出了PhNO/I共催化体系。
