铑催化的硫代重氮氧化吲哚与吲哚的碳-氢键插入反应

doi:10.6023/cjoc202604022

铑催化的硫代重氮氧化吲哚与吲哚的碳-氢键插入反应

崔效源^a,*, 闫宇慧^a, 宋毅彤^a, 石艺^a, 李雪^a, 牛慧^a, 计从斌^b,*

^a晋中学院化学化工系,山西晋中 030619;
^b上饶师范学院化学与环境科学学院,江西上饶 334001

收稿日期:2026-04-15 修回日期:2026-05-21
基金资助:
晋中学院博士专项基金、大学生创新训练计划（No.20251419）资助项目.

Rhodium-Catalyzed C-H Bond Insertion Reaction of Diazothiooxindoles with Indoles

Cui, Xiao-Yuan^a,*, Yan, Yu-Hui^a, Song Yi-Tong^a, Shi Yi^a, Li Xue^a, Ji, Cong-Bin^b,*

^aDepartment of Chemistry & Chemical Engineering, Jinzhong University, Jinzhong 030619;
^bSchool of Chemistry and Environmental Sciences, Shangrao Normal College, Shangrao 334001

Received:2026-04-15 Revised:2026-05-21
Contact: ^*E-mail: 19121715136@163.com; jcbpxh521@163.com
Supported by:
jinzhong University Research Funds for Doctor and Undergraduate Innovation Training Program（No.20251419）.

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摘要/Abstract

硫代氧化吲哚是一类非常重要的杂环骨架,广泛存在于天然产物和药物分子中。本文以硫代重氮氧化吲哚和吲哚为原料,在醋酸铑的催化下,成功合成了硫代氧化吲哚衍生物。采用¹H NMR、¹³C NMR以及高分辨质谱等技术对产物结构进行了表征,进行一系列条件探究之后发现该反应能够实现很好的区域选择性,以吲哚C3位选择性碳-氢键插入产物为主。同时,对产物进行了生物活性测试,包括：胚胎细胞、黑色素瘤细胞、乳腺癌细胞以及结肠癌细胞,结果表明产物具有一定程度的抗肿瘤活性。该反应具有条件简单,原子经济性高的特点。

关键词: 碳-氢键插入反应, 醋酸铑, 硫代氧化吲哚

Thiooxindole is a very important heterocyclic skeleton, which is widely found in natural products and pharmaceutical molecules. In this paper, thiooxindole derivatives were synthesized using diazothiooxindoles and indoles as raw materials under catalysis of rhodium acetate. After optimum reaction conditions were discussed, we found that C3-H bond insertion of indoles were main products with good regioselectivity. The structure of product was confirmed by ¹H NMR, ¹³C NMR, and HRMS. At the same time, activities of products were also tested, including NIH-3T3, B16-F10, 4T1 and HCT116. The results showed that the product exhibited a certain degree of antitumor activity. This reaction system has been proved simple to operate and atom-economic.

Key words: C-H bond insertion, rhodium acetate, thiooxindole

引用此文

崔效源, 闫宇慧, 宋毅彤, 石艺, 李雪, 牛慧, 计从斌. 铑催化的硫代重氮氧化吲哚与吲哚的碳-氢键插入反应[J]. 有机化学, doi: 10.6023/cjoc202604022.

Cui, Xiao-Yuan, Yan, Yu-Hui, Song Yi-Tong, Shi Yi, Li Xue, Ji, Cong-Bin. Rhodium-Catalyzed C-H Bond Insertion Reaction of Diazothiooxindoles with Indoles[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604022.

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