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

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Metal-free and Selectfluor-mediated diverse transformations of 2-alkylthiobenzamides to access 2,3-dihydrobenzothiazin-4-ones, benzoisothiazol-3-ones and 2-alkylthiobenzonitriles
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-06-14 , DOI: 10.1039/d2qo00663d
Shengfei Dai ₁ , Ke Yang ₁ , Yanqi Luo ₁ , Ziyuan Xu ₁ , Zhi Li ₁ , Zhengyi Li ₁ , Bijin Li ₂ , Xiaoqiang Sun ₁

Affiliation

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.

中文翻译：

无金属和 Selectfluor 介导的 2-烷基硫代苯甲酰胺的多种转化以获得 2,3-二氢苯并噻嗪-4-酮、苯并异噻唑-3-酮和 2-烷基硫代苯甲腈

已经建立了 2-烷基硫代苯甲酰胺的多种转化以在 Selectfluor 存在下合成 2,3-二氢苯并噻嗪-4-酮、苯并异噻唑-3-酮和 2-烷基硫基苯甲腈。NaI-HI 和 TFA-Ac ₂ O 系统都控制选择性 C-S 键断裂和 C-H 键官能化以获取 2,3-二氢苯并噻嗪-4-酮和 2-取代的 2,3-二氢苯并噻嗪-4-酮，分别。值得注意的是，这是使用 Selectfluor 作为亚甲基源构建重要的 2,3-二氢苯并噻嗪-4-酮的第一个例子。在 HCl 存在下，苯并异噻唑-3-酮以良好的收率获得。此外，2-烷基硫代苄腈也可以使用相同的 NaI-HI 系统通过硫醚定向和 Selectfluor 介导的 2-烷基硫代苯甲酰胺脱水。

更新日期：2022-06-14

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