文献类型：期刊文献

英文题名：Iodine-Catalyzed Cyclization of o-Nitrothiophenols with Cyclohexanones to Phenothiazines

作者：Zhao, Yinglin[1,2];Zhang, Jin[1,2];Zhang, Jingwu[3];Zhang, Zhida[1,2];Liu, Renhua[1,2]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Minist Educ, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[3]Shandong Med Techn Coll, Tai An 271000, Shandong, Peoples R China

年份：2024

卷号：89

期号：11

起止页码：7478

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20242216152489);WOS:【SCI-EXPANDED(收录号:WOS:001229477500001)】；

基金：We gratefully acknowledge the National Natural Science Foundation of China (grant 21072055) for financial support of this work.

语种：英文

外文关键词：Catalysis - Hydrogen - Insecticides - Iodine

摘要：Here, a novel iodine-catalyzed direct cyclization of o-nitrothiophenols with cyclohexanones to phenothiazines has been described without external oxidants and hydrogen acceptors. The nitro of o-nitrothiophenol works as both a hydrogen acceptor and a coupling group, and water is the only byproduct. The reaction involves the reduction of nitro groups, C-H bond thioetherification, and C-H bond dehydroaromatization. This scheme offers broad synthetic value for further elaborations, as exemplified by a 3-step total synthesis of antipsychotic chlorpromazine.