无过渡金属催化条件下合成3,3'-二吲哚甲烷衍生物的最新进展

doi:10.6023/cjoc202008003

有机化学 ›› 2021, Vol. 41 ›› Issue (1): 52-64.DOI: 10.6023/cjoc202008003 上一篇下一篇

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无过渡金属催化条件下合成3,3'-二吲哚甲烷衍生物的最新进展

张振国^a, 刘笑笑^a, 宗鑫龙^a, 苑亚林^a, 刘双磊^a, 张婷^a, 吴子尚^a, 杨静莹^*(), 贾振华^a^,^*()

a 南京工业大学化学与分子工程学院先进化学制造研究院南京 211816

收稿日期:2020-08-05 修回日期:2020-10-13 发布日期:2020-10-22
通讯作者: 杨静莹, 贾振华
作者简介:
* Corresponding authors. E-mail: iasjyyang@njtech.edu.cn; iaszhjia@njtech.edu.cn
基金资助:
南京工业大学启动基金(38037037); 江苏省协同联合创新中心和江苏省研究生科研与实践创新计划(KYCX20_1031)

Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions

Zhenguo Zhang^a, Xiaoxiao Liu^a, Xinlong Zong^a, Yalin Yuan^a, Shuanglei Liu^a, Ting Zhang^a, Zishang Wu^a, Jingying Yang^*(), Zhenhua Jia^a^,^*()

1 Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816

Received:2020-08-05 Revised:2020-10-13 Published:2020-10-22
Contact: Jingying Yang, Zhenhua Jia
Supported by:
the Start-up Grant of Nanjing Tech University(38037037); the Synergetic Innovation Center for Advanced Materials Fellowship and Postgraduate Research & Practice Innovation Program of Jiangsu Province(KYCX20_1031)

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摘要/Abstract

3,3'-二吲哚甲烷类化合物是一类重要的吲哚生物碱, 其结构单元广泛存在于天然产物、功能性材料以及合成药物分子中. 因其具有多样的生物活性和功能, 如抗氧化、抗炎症、抗血管生成、抗菌以及抗癌活性等, 构筑3,3'-二吲哚甲烷类杂环化合物备受关注. 传统的合成方法, 尤其是对称结构的3,3'-二吲哚甲烷类化合物的合成主要在化学量的Brønsted酸或Lewis酸存在下, 吲哚衍生物与羰基化合物经傅-克反应缩合得到. 而过渡金属的使用可引起化合物中金属残留以及环境污染. 总结和探讨了从2010年至今3,3'-二吲哚甲烷类化合物的合成方法, 尤其是对无过渡金属参与条件下, 对称结构的3,3'-二吲哚甲烷类化合物以及非对称结构3,3'-二吲哚甲烷类化合物制备的最新进展以及相应的反应机理, 旨在为该类化合物生物活性测试提供重要的理论依据和技术支持.

关键词: 无过渡金属, 3, 3'-二吲哚甲烷, 生物活性, 多样性

3,3'-Bisindolylmethanes (3,3'-BIMs) compounds are important indole alkyloads and their units are widely found in various natural products, functional materials and synthetic pharmaceutical compounds. Due to diverse biological activities and functionalities, for instance, antioxidant, anti-inflammatory, antiangiogenic, anti-bacterial and anti-cancer etc., the construction of 3,3'-BIMs is raised considerable concerns. Conventional methods especially focused on symmetrical 3,3'-BIMs were the condensition of indoles with carbonyl compounds via Friedel-Crafts pathway in the presence of Brønsted acids or Lewis acids. However, the utilization of transtion metals led the residue into the products and environmental contamination. The recent advance on the synthesis of 3,3'-BIMs since 2010, mainly concerned on the approaches and corresponding me- chanism to prepare symmetrical and unsymmetrical 3,3'-BIMs under transition-metal-free conditions is summarized and dis- cussed, aiming to provide important theoretical evidence and techinical support for further biological evaluations on desired compounds.

Key words: Keywords transition-metal-free, 3, 3'-bisindolylmethane, biological activity, diversity

引用此文

张振国, 刘笑笑, 宗鑫龙, 苑亚林, 刘双磊, 张婷, 吴子尚, 杨静莹, 贾振华. 无过渡金属催化条件下合成3,3'-二吲哚甲烷衍生物的最新进展[J]. 有机化学, 2021, 41(1): 52-64.

Zhenguo Zhang, Xiaoxiao Liu, Xinlong Zong, Yalin Yuan, Shuanglei Liu, Ting Zhang, Zishang Wu, Jingying Yang, Zhenhua Jia. Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 52-64.

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图/表 27

Scheme 1. Representative nature products and synthetic compounds containing 3,3'-BIMs units

Scheme 2. General Friedel-Crafts pathway to achieve symmetrical 3,3'-BIMs

Scheme 3. Huo’s synthesis of symmetrical 3,3'-BIMs by recyclable process

Scheme 4. Taha’s synthesis sequential route of bisindolylmethane-hydrazone hybrids

Scheme 5. Anbarsasan’s synthesis of trifluoromethylated bis(indolyl)arylmethanes

Scheme 6. Zhong’s B(C6F5)3-catalyzed synthesis of the symmetrical 3,3'-BIMs

Scheme 7. He’s B(C6F5)3-catalyzed reductive synthesis of the symmetrical 3,3'-BIMs

Scheme 8. Huo’s Friedel-Crafts alkylation initiated by triarylaminium salt

Scheme 9. Toy’s synthesis of the symmetrical 3,3'-BIMs by halogen bond catalyzed strategy

Scheme 10. Halimehjani’s tetra-cationic acidic organic salts (TCAOS)

Scheme 11. Itoh’s photo-induced I2-catalyzed synthesis of symmetrical 3,3'-BIMs in O2 atmosphere

Scheme 12. Singh’s organo-photo-catalyst mediated synthesis of symmetrical 3,3'-BIMs

Scheme 13. Xia’s photo-redox synthesis of symmetrical 3,3'-BIMs

Scheme 14. Qiu’s CF3SO2Na-induced synthesis of symmetrical 3,3'-BIMs

Scheme 15. Ning’s Br2-catalyzed synthesis of symmetrical 3,3'-BIMs

Scheme 16. Zhang’s fiber-supported ILs-catalyzed synthesis of symmetrical 3,3'-BIMs

Scheme 17. Arai’s 2-iodoimidazolinium salt-catalyzed synthesis of symmetrical 3,3'-BIMs

Scheme 18. Yamajala’s VB1-catalyzed synthesis of symmetrical 3,3'-BIMs

Scheme 19. Wang’s graphene oxide-catalyzed synthesis of symmetrical 3,3'-BIMs

Scheme 20. General strategy for the synthesis of unsymmetrical 3,3'-BIMs

Scheme 21. Sigman’sp-TsOH catalyzed synthesis of unsymmetrical 3,3'-BIMs

Scheme 22. Sasaki’s synthesis of trifluoromethyl-functionalized unsymmetrical 3,3'-BIMs

Scheme 23. Xiao’s synthesis of unsymmetrical 3,3'-BIMs in water

Scheme 24. Mu?ller’s synthesis of unsymmetrical 3,3'-BIMs in water

Scheme 25. You’s the first enantioselective synthesis of chiral 3,3'-BIMs

Scheme 26. Zhang’s enantioselective synthesis of chiral 3,3'- BIMs

Scheme 27. Kim’s chiral phosphoric acid catalytic synthesis of chiral 3,3'-BIMs sulfamate derivatives

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无过渡金属催化条件下合成3,3'-二吲哚甲烷衍生物的最新进展

Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions

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