Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles

被引：0
|
作者：
Dai, Shengfei [1 ]
Yang, Ke [1 ]
Luo, Yanqi [1 ]
Xu, Ziyuan [1 ]
Li, Zhi [1 ]
Li, Zhengyi [1 ]
Li, Bijin [2 ]
Sun, Xiaoqiang [1 ]
机构：
[1] Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Jiangsu, Changzhou,213164, China
[2] Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing,401331, China
来源：
Organic Chemistry Frontiers | 2022年 / 9卷 / 15期
基金：
中国国家自然科学基金;
关键词：
Iodine compounds - Sodium Iodide;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Diverse transformations of 2-alkylthiobenzamides have been established to synthesize 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles in the presence of Selectfluor. Both NaI-HI and TFA-Ac2O systems control the selective C-S bond cleavage and C-H bond functionalization to access 2,3-dihydrobenzothiazin-4-ones and 2-substituted 2,3-dihydrobenzothiazin-4-ones, respectively. Notably, this is the first example of using Selectfluor as a methylene source to construct important 2,3-dihydrobenzothiazin-4-ones. In the presence of HCl, benzoisothiazol-3-ones were obtained in good yields. Furthermore, 2-alkylthiobenzonitriles could also be prepared using the same NaI-HI system via a thioether-directed and Selectfluor-mediated dehydration of 2-alkylthiobenzamides. © 2022 The Royal Society of Chemistry.
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页码：4016 / 4022
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