SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 1: 75 - 84

DOI: https://doi.org/10.6023/cjoc202107012

综述与进展

吲哚氮杂环作为自由基受体在串联环化反应中的研究进展

  • 王弯弯 ,
  • 张明明 ,
  • 杨文超 ,
  • 杨小虎
展开
  • a 泰州学院医药与化学化工学院 江苏泰州 225300
    b 扬州大学园艺与植物保护学院 江苏扬州 225009
    c 浙江医院药剂科 杭州 310013

收稿日期: 2021-07-05

  修回日期: 2021-09-01

  网络出版日期: 2021-09-08

基金资助

江苏省高校自然科学基金(19KJB150020)

收起

Research Progress in Radical Cascade Reaction Using Nitrogen Heterocycle in Indoles as Radical Acceptors

  • Wanwan Wang ,
  • Mingming Zhang ,
  • Wenchao Yang ,
  • Xiaohu Yang
Expand
  • a College of Pharmacy and Chemistry & Chemical Engineering, Taizhou University, Taizhou, Jiangsu 225300
    b School of Horticulture and Plant Protection, Yangzhou University, Yangzhou, Jiangsu 225009
    c Department of Pharmacy, Zhejiang Hospital, Hangzhou 310013
* Corresponding authors. E-mail: ;

Received date: 2021-07-05

  Revised date: 2021-09-01

  Online published: 2021-09-08

Supported by

Natural Science Foundation of the Jiangsu Higher Education Institutions of China(19KJB150020)

Fold

摘要

含吲哚骨架衍生物因其具有多样的生物活性, 广泛应用于生物活性分子的合成与修饰, 特别是在药物化学、农药化学领域中. 近年来, 高效的吲哚环合成与后官能化反应已成为热门的研究主题, 例如吲哚的不对称去芳构化反应构建螺环衍生物. 不饱和烃的自由基串联反应一直是有机化学的一个重要研究分支, 含吲哚母体的不饱和烃串联环化反应已经成为吲哚骨架修饰的一种重要途径. 因此, 综述了吲哚骨架中氮杂环作为自由基受体在不饱和烃串联环化反应中的研究进展, 并对反应设计、机理研究、研究展望等给予评述.

关键词： 吲哚; 自由基; 串联环化反应; 不饱键; 双官能化

本文引用格式

王弯弯 , 张明明 , 杨文超 , 杨小虎 . 吲哚氮杂环作为自由基受体在串联环化反应中的研究进展[J]. 有机化学, 2022 , 42(1) : 75 -84 . DOI: 10.6023/cjoc202107012

Abstract

Indole skeleton has been widely utilized in the synthesis and late-stage modification of biologically active compounds, especially in the fields of medicines and pesticides. In recent years, constructing spiro compounds by asymmetric dearomatization of indoles has become extremely promising. Meanwhile, the radical tandem reaction of unsaturated bonds has been a significant branch of organic chemistry, and this methodology has become a crucial approach to modify the indole skeleton. Therefore, the recent progress in the field of radical cascade reaction of unsaturated hydrocarbon using nitrogen heterocycle in indoles as radical acceptors is summarized. Besides, the reaction design, mechanism and prospects of this field are also discussed.

Key words： indole; radical; cascade cyclization reactions; unsaturated bonds; difunctionalization

参考文献

[1]
(a) Oishi, S.; Watanabe, T.; Sawada, J.; Asai, A.; Ohno, H.; Fujii, N. J. Med. Chem. 2010, 53, 5054.
[1]
(b) Mahmoud, M. M.; Ali, H. I.; Ahn, K. H.; Damaraju, A.; Samala, S.; Pulipati, V. K.; Kolluru, S.; Kendall, D. A.; Lu, D. J. Med. Chem. 2013, 56, 7965.
[2]
(a) Xiao, Z.; Wang, L.; Wei, J.; Ran, C.; Liang, S.; Shang, J.; Chen, G.-Y.; Zheng, C. Chem. Commun. 2020, 56, 4164.
[2]
(b) Wang, D., https://mp.weixin.qq.com/s/U8FVSkdON-eKo7rUcu7kQw.
[2]
(c) Shi, Z.; Nie, K.; Liu, C.; Zhang, M.; Zhang, W. Chin. J. Org. Chem. 2020, 40, 327. (in Chinese)
[2]
(施展, 聂克睿, 刘畅, 张明智, 章维华, 有机化学, 2020, 40, 327.)
[3]
(a) Huang, G.; Yin, B. Adv. Synth. Catal. 2019, 361, 405.
[3]
(b) Lü, S.; Zhang, G.; Chen, J.; Gao, W. Adv. Synth. Catal. 2020, 362, 462.
[4]
(a) Yang, W.-C.; Feng, J.-G.; Wu, L.; Zhang, Y.-Q. Adv. Synth. Catal. 2019, 361, 1700.
[4]
(b) Yang, W.-C.; Zhang, M.-M.; Feng, J.-G. Adv. Synth. Catal. 2020, 362, 4446.
[4]
(c) Shang, T.; Lu, L.; Cao, Z.; Liu, Y.; He, W.; Yu, B. Chem. Commun. 2019, 55, 5408.
[4]
(d) Wu, Y.; Chen, J.-Y.; Li, Q.; Wei, W.-T. Chin. J. Org. Chem. 2020, 40, 589. (in Chinese)
[4]
(吴燕, 陈锦杨, 李强, 魏文廷, 有机化学, 2020, 40, 589.)
[4]
(e) Zhang, M.; Shen, L.; Dong, S.; Li, B.; Meng, F.; Si, W.; Yang, W. Eur. J. Org. Chem. 2021, 31, 4465.
[5]
(a) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505.
[5]
(b) Lei, J.; Huang, J.; Zhu, Q. Org. Biomol. Chem. 2016, 14, 2593.
[5]
(c) Song, B.; Xu, B. Chem. Soc. Rev. 2017, 46, 1103.
[5]
(d) Yang, W.-C.; Wei, K.; Sun, X.; Zhu, J.; Wu, L. Org. Lett. 2018, 20, 3144.
[5]
(e) Liu, Y.; Chen, X.-L.; Sun, K.; Li, X.-Y.; Zeng, F.-L.; Liu, X.-C.; Qu, L.-B.; Zhao, Y.-F.; Yu, B. Org. Lett. 2019, 21, 4019.
[6]
He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451.
[7]
Han, G.; Wang, Q.; Chen, L.; Liu, Y.; Wang, Q. Adv. Synth. Catal. 2016, 358, 561.
[8]
(a) Yang, W.; Yang, S.; Li, P.; Wang, L. Chem. Commun. 2015, 51, 7520.
[8]
(b) Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China Chem. 2019, 62, 24.
[8]
(c) Liu, Y.; Lin, L.; Han, Y.; Liu, Y. Chin. J. Org. Chem. 2020, 40, 4216. (in Chinese)
[8]
(刘洋, 林立青, 韩莹徽, 刘颖杰, 有机化学, 2020, 40, 4216.)
[8]
(d) Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese)
[8]
(杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.)
[8]
(e) He, S.-Q.; Li, H.-C.; Chen, X.-L.; Krylov, I. B.; Terent’ev, A. O. Qu, L.-B.; Yu, B. Chin. J. Org. Chem. 2021, 41, 4661. (in Chinese)
[8]
(贺帅旗, 李昊聪, 陈晓岚, Igor B. Krylov, Alexander O. Terent'ev, 屈凌波, 於兵, 有机化学, 2021, 41, 4661.)
[8]
(f) Yang, W.-C.; Zhang, M.-M.; Sun, Y.; Chen, C.-Y.; Wang, L. Org. Lett. 2021, 23, 6691.
[9]
Zhu, M.; Zhou, K.; Zhang, X.; You, S.-L. Org. Lett. 2018, 20, 4379.
[10]
Qin, W.-B.; Xiong, W.; Li, X.; Chen, J.-Y.; Lin, L.-T.; Wong, H. N. C.; Liu, G.-K. J. Org. Chem. 2020, 85, 10479.
[11]
Liu, Y.; Chen, Z.; Wang, Q.-L.; Chen, P.; Xie, J.; Xiong, P.-Q.; Zhang, P.-L.; Tang, K.-W. J. Org. Chem. 2020, 85, 2385.
[12]
(a) Penteado, F.; Lopes, E. F.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardão, E. J. Chem. Rev. 2019, 119, 7113.
[12]
(b) Yang, W.-C.; Dai, P.; Luo, K.; Ji, Y.-G.; Wu, L. Adv. Synth. Catal. 2017, 359, 2390.
[12]
(c) Zhu, H.-L.; Zeng, F.-L.; Chen, X.-L.; Sun, K.; Li, H.-C.; Yuan, X.-Y.; Qu, L.-B.; Yu, B. Org. Lett. 2021, 23, 2976.
[12]
(d) Ji, W.; Tan, H.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2016, 52, 1462.
[12]
(e) Xu, N.; Li, P.; Xie, Z.; Wang, L. Chem.-Eur. J. 2016, 22, 2236.
[12]
(f) Li, D.; Wang, M.; Liu, J.; Zhao, Q.; Wang, L. Chem. Commun. 2013, 49, 3640.
[12]
(g) Reddy, C. R.; Kajareab, R. C.; Punna, N. Chem. Commun. 2020, 56, 3445.
[13]
(a) Zhang, Y.; Sun, K.; Lü, Q.; Chen, X.; Qu, L.; Yu, B. Chin. Chem. Lett. 2019, 30, 1361.
[13]
(b) Xu, J.; Zhang, S.; Luo, Y.; Zhang, L.; Zhang, F.; Huang, T.; Song, Q. Acta Chim. Sinica 2019, 77, 932. (in Chinese)
[13]
(许健, 张世樊, 罗莹, 张荔, 张帆, 黄挺菁, 宋秋玲, 化学学报, 2019, 77, 932.)
[13]
(c) Liu, X.-C.; Chen, X.-L.; Liu, Y.; Sun, K.; Peng, Y.-Y.; Qu, L.-B.; Yu, B. ChemSusChem 2020, 13, 298.
[14]
Li, C.; Xue, L.; Zhou, J.; Zhao, Y.; Han, G.; Hou, J.; Song, Y.; Liu, Y. Org. Lett. 2020, 22, 3291.
[15]
(a) Luo, K.; Yang, W.-C.; Wu, L. Asian J. Org. Chem. 2017, 6, 350.
[15]
(b) Jing, C.; Chen, X.; Sun, K.; Yang, Y.; Chen, T.; Liu, Y.; Qu, L.; Zhao, Y.; Yu, B. Org. Lett. 2019, 21, 486.
[15]
(c) Zhou, Z.-Z.; Jin, D.-P.; Li, L.-H.; He, Y.-T.; Zhou, P.-X.; Yan, X.-B.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2014, 16, 5616.
[15]
(d) Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972.
[16]
(a) Liu, J. M.; Zhao, S. S.; Song, W. W.; Li, R.; Guo, X. Y.; Zhuo, K. L.; Yue, Y. Y. Adv. Synth. Catal. 2017, 359, 609.
[16]
(b) Xu, J.; Yu, X.; Song, Q. Org. Lett. 2017, 19, 980.
[17]
Gorre, R.; Enagandhula, D.; Balasubramanianbc, S.; Akondi, S. M. Org. Biomol. Chem. 2020, 18, 1354.
[18]
(a) Chen, S.; Zhang, P. B.; Shu, W. Y.; Gao, Y. Z.; Tang, G.; Zhao, Y. F. Org. Lett. 2016, 18, 5712.
[18]
(b) Zhang, H.; Li, W.; Zhu, C. J. Org. Chem. 2017, 82, 2199.
[19]
Hua, H.-L.; Zhang, B.-S.; He, Y.-T.; Qiu, Y.-F.; Wu, X.-X.; Xu, P.-F.; Liang, Y.-M. Org. Lett. 2016, 18, 216.
[20]
(a) Zhu, J.; Yang, W.-C.; Wang, X.-D.; Wu, L. Adv. Synth. Catal. 2018, 360, 386.
[20]
(b) Zhang, M.-M.; Sun, Y.; Wang, W.-W.; Chen, K.-K.; Yang, W.-C.; Wang, L. Org. Biomol. Chem. 2021, 19, 3844.
[20]
(c) Zhang, P.; Gao, Y.; Chen, S.; Tang, G.; Zhao, Y. Org. Chem. Front. 2017, 4, 1350.
[20]
(d) Xie, X.; Li, P.; Wang, L. Eur. J. Org. Chem. 2019, 221.
[20]
(e) Chen, H.; Liu, M.; Qiu, G.; Wu, J. Adv. Synth. Catal. 2019, 361, 146.
[20]
(f) Zhang, P.; Shi, S.; Gao, X.; Han, S.; Lin, J.; Zhao, Y. Org. Biomol. Chem. 2019, 17, 2873.
[20]
(g) Shen, Z.-J.; Huang, B.; Ma, N.; Yao, L.; Yang, C.; Guo, L.; Xia, W. Adv. Synth. Catal. 2021, 363, 1944.
[21]
Zhu, J.; Sun, S.; Xia, M.; Gu, N.; Cheng, J. Org. Chem. Front. 2017, 4, 2153.
[22]
Zhu, X.-Y.; Han, Y.-P.; Li, M.; Li, X.-S.; Liang, Y.-M. Adv. Synth. Catal. 2018, 360, 3460.
[23]
Gharpure, S. J.; Shelke, Y. G. Org. Lett. 2017, 19, 5022.
[24]
(a) Ho, H. E.; Pagano, A.; Rossi-Ashton, J. A.; Donald, J. R.; Epton, R. G.; Churchill, J. C.; James, M. J.; O'Brien, P.; Taylor, R. J. K.; Unsworth, W. P. Chem. Sci. 2020, 11, 1353.
[24]
(b) Zhou, X.-J.; Liu, H.-Y.; Mo, Z.-Y.; Ma, X.-L.; Chen, Y.-Y.; Tang, H.-T.; Pan, Y.-M.; Xu, Y.-L. Chem.-Asian J. 2020, 15, 1536.
[25]
Sun, K.; Chen, X. L.; Zhang, Y. L.; Li, K.; Huang, X. Q.; Peng, Y. Y.; Qu, L. B.; Yu, B. Chem. Commun. 2019, 55, 12615.
Options
文章导航

/

〈 〉