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Transition-metal-free skeletal editing of benzoisothiazol-3-ones to 2,3-dihydrobenzothiazin-4-ones via single-carbon insertion
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-11-07 , DOI: 10.1039/d4qo01714e
Ke Yang, Qin Li, Yanqi Luo, Dan Yuan, Chunjian Qi, Zhengyi Li, Bijin Li, Xiaoqiang Sun

Transition-metal-free ring expansion of benzoisothiazol-3-ones has been established to synthesize 2,3-dihydrobenzothiazin-4-ones via single-carbon insertion. A variety of 2,3-dihydrobenzothiazin-4-ones have been prepared with good yields. The use of aldehydes and ketones resulted in the formation of 2-substituted and 2,2-disubstituted 2,3-dihydrobenzothiazin-4-ones using HI and NH4I as additives. Furthermore, the easily prepared 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride [DABCO·DCM] was first utilized as the methylene source for the selective synthesis of 2,3-dihydrobenzothiazin-4-ones and bis-2,3-dihydrobenzothiazin-4-ones.

中文翻译:


通过单碳插入将苯并异噻唑-3-酮转化为 2,3-二氢苯并噻嗪-4-酮的无过渡金属骨架编辑



已经建立了苯并异噻唑-3-酮的无过渡金属扩环,以通过单碳插入合成 2,3-二氢苯并噻嗪-4-酮。已经制备了多种 2,3-二氢苯并噻嗪-4-酮,收率良好。醛和酮的使用导致使用 HI 和 NH4I 作为添加剂形成 2-取代和 2,2-二取代 2,3-二氢苯并噻嗪-4-酮。此外,易于制备的 1-(氯甲基)-1,4-二氮杂双环[2.2.2]辛烷-1-氯化铵 [DABCO·DCM] 首先被用作亚甲基源,用于选择性合成 2,3-二氢苯并噻嗪-4-酮和双-2,3-二氢苯并噻嗪-4-酮。
更新日期:2024-11-12
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