Palladium-Catalyzed Aminosulfonylation of <i>ortho</i>-Iodoanilines with the Insertion of Sulfur Dioxide for the Synthesis of 3,4-Dihydro-benzothiadiazine 1,1-Dioxides
Zhenjie QiDepartment of Engineering, Jining University, Qufu, Shandong 273155, P. R. ChinaSimiaomiao WenHunan Provincial Key Laboratory of the Research and Development of Novel Pharmaceutical Preparations, Changsha Medical University, Provincial First-Class Applied Discipline (Pharmacy), Changsha, 410219, ChinaHao LiDepartment of Engineering, Jining University, Qufu, Shandong 273155, P. R. ChinaShuai LiuSchool of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou 221018, ChinaDongfang JiangHunan Provincial Key Laboratory of the Research and Development of Novel Pharmaceutical Preparations, Changsha Medical University, Provincial First-Class Applied Discipline (Pharmacy), Changsha, 410219, China
2023en
ABI
Аннотация
A simple and efficient Pd-catalyzed oxidative cyclization system is developed for the chemo- and regioselective synthesis of 3,4-dihydro-benzothiadiazine 1,1-dioxides, which are formed through aminosulfonylation of ortho-iodoanilines with SO2. DABSO is utilized as the source of SO2, and the organic compound O2 acts as an oxidant. This direct C–S, S–N, and C–N functionalization is highly efficient, and broad functional group tolerance is observed, resulting in moderate to excellent yields of 3,4-dihydro-benzothiadiazine 1,1-dioxides. Furthermore, this method is amenable to gram-scale synthesis.
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