SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 7: 2293 - 2303

DOI: https://doi.org/10.6023/cjoc202304014

REVIEWS

Research Progress in Synthesis of Spirocyclic Compounds Driven by Photo/Electrochemistry

  • Ning Chen ,
  • Chengdong Zhang ,
  • Peng Li ,
  • Ge Qiu ,
  • Yinjie Liu ,
  • Tianlei Zhang
Expand
  • aSchool of Pharmacy, Harbin University of Commerce, Harbin 150076
    bHeilongjiang Nursing College, Harbin 150086
    cSchool of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005
*E-mail: ;

Received date: 2023-04-10

  Revised date: 2023-06-05

  Online published: 2023-06-26

Supported by

Heilongjiang Postdoctoral Scientific Research Development Fund(LBH-Q20103); the Construction and Cultivation Project of Collaborative Innovation Achievements of University Disciplines(LJGXCG2022-086)

Fold

Abstract

As important organic molecular frameworks, spirocycles exist widely in organic chemistry, medicinal chemistry, material science and other fields. Since the spirocyclic skeleton has a large three-dimensional space structure, which meets the demand for conformational rigidity in drug design, it is particularly important to develop efficient synthetic methods for spirocyclic compounds. In recent years, photocatalysis and electrocatalysis have injected new potential into the synthesis of spirocyclic compounds as green and efficient synthetic methods. This article is mainly classified by the construction of snail [4.5] skeleton, snail [5.5] skeleton, snail [2.3] skeleton, and spiro-indoles skeleton. Moreover, the construction of spirocyclic compounds is reviewed from two aspects: photocatalysis and electrocatalytic synthesis.

Key words： spirocycles; photocatalysis

Cite this article

Ning Chen , Chengdong Zhang , Peng Li , Ge Qiu , Yinjie Liu , Tianlei Zhang . Research Progress in Synthesis of Spirocyclic Compounds Driven by Photo/Electrochemistry[J]. Chinese Journal of Organic Chemistry, 2023 , 43(7) : 2293 -2303 . DOI: 10.6023/cjoc202304014

References

[1]
Hu, J. F.; Fan, H.; Xiong, J.; Wu, S. B. Chem. Rev. 2011, 111, 5465.
[2]
Wu, W. T.; Zhang, L.; You, S. L. Chem. Soc. Rev. 2016, 45, 1570.
[3]
Liang, X. W.; Zheng, C.; You, S. L. Chem.-Eur. J. 2016, 22, 11918.
[4]
Gao, Y.-R.; Tong, H.-J.; Zhao, M.-M.; Du, M.; Tang, W.-Q. Fine Spec. Chem. 2022, 30, 37 (in Chinese).
[4]
(高艳蓉, 仝红娟, 赵梅梅, 杜漠, 唐文强, 精细与专用化学品, 2022, 30, 37.)
[5]
Yu, B.; Yu, Z.; Qi, P. P.; Yu, D. Q.; Liu, H. M. Eur. J. Med. Chem. 2015, 95, 35.
[6]
Mani, K. S.; Kaminsky, W.; Rajendran, S. P. New J. Chem. 2018, 42, 301.
[7]
Yang, Y. T.; Zhu, J. F.; Liao, G.; Xu, H. J.; Yu, B. Curr. Med. Chem. 2018, 25, 2233.
[8]
de Candia, M.; Altamura, C.; Denora, N.; Cellamare, S.; Nuzzolese, M.; De Vito, D.; Voskressensky, L. G.; Varlamov, A. V.; Altomare, C. D. Chem. Heterocycl. Compd. 2017, 53, 357.
[9]
Barakat, A.; Soliman, S. M.; Al-Majid, A. M.; Ali, M.; Islam, M. S.; Elshaier, Y. A.; Ghabbour, H. A. J. Mol. Struct. 2018, 1152, 101.
[10]
Cacho, R. A.; Chooi, Y. H.; Zhou, H.; Tang, Y. ACS Chem. Biol. 2013, 8, 2322.
[11]
Saraswat, P.; Jeyabalan, G.; Hassan, M. Z.; Rahman, M. U.; Nyola, N. K. Synth. Commun. 2016, 46, 1643.
[12]
Cheng, X.; Gao, P.; Sun, L.; Tian, Y.; Zhan, P.; Liu, X. Expert Opin. Ther. Pat. 2017, 27, 1277.
[13]
Yang, W. C.; Zhang, M. M.; Feng, J. G. Adv. Synth. Catal. 2020, 362, 4446.
[14]
Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102.
[15]
Griesbeck, A. G. Beilstein J. Org. Chem. 2014, 10, 1097.
[16]
Talele, T. T. J. Med. Chem. 2020, 63, 13291.
[17]
Hiesinger, K.; Dar’in, D.; Proschak, E.; Krasavin, M. J. Med. Chem. 2020, 64, 150.
[18]
Yugandhar, D.; Nayak, V. L.; Archana, S.; Shekar, K. C.; Srivastava, A. K. Eur. J. Med. Chem. 2015, 101, 348.
[19]
Cai, Y. S.; Guo, Y. W.; Krohn, K. Nat. Prod. Rep. 2010, 27, 1840.
[20]
Hu, B.; Li, Y.; Dong, W.; Ren, K.; Xie, X.; Wan, J.; Zhang, Z. Chem. Commun. 2016, 52, 3709.
[21]
Han, Y.; Jin, Y.; Jiang, M.; Yang, H.; Fu, H. Org. Lett. 2019, 21, 1799.
[22]
Li, H.; Subbotina, E.; Bunrit, A.; Wang, F.; Samec, J. S. Chem. Sci. 2019, 10, 3681.
[23]
Flynn, A. R.; McDaniel, K. A.; Hughes, M. E.; Vogt, D. B.; Jui, N. T. J. Am. Chem. Soc. 2020, 142, 9163.
[24]
Zhou, C.; Shatskiy, A.; Temerdashev, A. Z.; K?rk?s, M. D.; Dinér, P. Chem. Commun. 2022, 5, 92.
[25]
Yang, M.; Hua, J.; Wang, H.; Ma, T.; Liu, C. K.; He, W.; Zhu, N.; Hu, Y. J.; Fang, Z.; Guo, K. J. Org. Chem. 2022, 87, 8445.
[26]
Liu, F. L.; Mei, L.; Wang, L. T.; Zhou, Y.; Tang, K. Q.; Li, T.; Yi, R. N.; Wei, W. T. Chem. Commun. 2023, 59, 6391.
[27]
Li, L.; Li, J. Z.; Sun, Y. B.; Luo, C. M.; Qiu, H.; Tang, K. Q.; Liu, H. X.; Wei, W. T. Org. Lett. 2022, 24, 4704.
[28]
Wang, D. K.; Li, L. B.; Liu, F. L.; Qiu, H.; Li, J. Z.; Zhang, J. F.; Deng, C.; Wei, W. T. ACS Cent. Sci. 2022, 8, 1028.
[29]
Sun, K.; Zhao, D. Y.; Li, Q. X.; Ni, S. F.; Zheng, G. F.; Zhang, Q. Sci. China: Chem. 2023, DOI: 10.1007/s11426-023-1622-1.
[30]
Wei, W.; Cui, H. H.; Yang, D. S.; Yue, H. L.; He, C. L.; Zhang, Y. L.; Wang, H. Green Chem. 2017, 19, 5608.
[31]
Dong, W. H.; Yuan, Y.; Gao, X. S.; Keranmu, M.; Li, W. F.; Xie, X. M.; Zhang, Z. G. Org. Lett. 2018, 20, 5762.
[32]
Dong, W. H.; Yuan, Y.; Gao, X. S.; Keranmu, M.; Li, W. F.; Xie, X. M.; Zhang, Z. G. J. Org. Chem. 2019, 84, 1461.
[33]
Dong, W. H.; Yuan, Y.; Xie, X. M.; Zhang, Z. G. Org. Lett. 2020, 22, 528.
[34]
Dong, W. H.; Yuan, Y.; Liang, C. Y.; Wu, F.; Zhang, S. Y.; Xie, X. M.; Zhang, Z. G. J. Org. Chem. 2021, 86, 3697.
[35]
Dong, W. H.; Yuan, Y.; Gao, X. S.; Keranmu, M., Li, W. F.; Xie, X. M.; Zhang, Z. G. Org. Lett. 2018, 20, 5762.
[36]
Liu, Y.; Wang, Q. L.; Chen, Z.; Zhou, Q.; Xiong, B. Q.; Zhang, P. L.; Tang, K. W. Chem. Commun. 2019, 55, 12212.
[37]
Ouyang, X. H.; Song, R. J.; Li, Y.; Liu, B.; Li, J. H. J. Org. Chem. 2014, 79, 4582.
[38]
Wei, W. T.; Song, R. J.; Ouyang, X. H.; Li, Y.; Li, H. B.; Li, J. H. Org. Chem. Front. 2014, 1, 484.
[39]
Wang, L. J.; Wang, A. Q.; Xia, Y.; Wu, X. X.; Liu, X. Y.; Liang, Y. M. Chem. Commun. 2014, 50, 13998.
[40]
Wu, L. J.; Tan, F. L.; Li, M.; Song, R. J.; Li, J. H. Org. Chem. Front. 2017, 4, 350.
[41]
Yuan, Y. Q.; Kumar, P. S.; Zhang, C. N.; Yang, M. H.; Guo, S. R. Org. Biomol. Chem. 2017, 15, 7330.
[42]
Yang, X. H.; Ouyang, X. H.; Wei, W. T.; Song, R. J.; Li, J. H. Adv. Synth. Catal. 2015, 357, 1161.
[43]
Zhang, N.; Zuo, H.; Xu, C.; Pan, J.; Sun, J.; Guo, C. Chin. Chem. Lett. 2020, 31, 337.
[44]
Liu, T.; Li, Y. M.; Jiang, L. L.; Wang, J. A.; Jin, K.; Zhang, R.; Duan, C. Y. Org. Biomol. Chem. 2020, 18, 1933.
[45]
Chung, W. J.; Vanderwal, C. D. Angew. Chem., nt. Ed. 2016, 55, 4396.
[46]
Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937.
[47]
Chen, Y.; Lu, F. Y.; Li, R. X.; Guan, Z.; He, Y. H. Asian J. Org. Chem. 2021, 10, 668.
[48]
Yuan, J. W.; Shen, L.; Ma, M. Y.; Feng, S.; Yang, W.; Yang, L. R.; Xiao, Y. M.; Zhang, S. R.; Qu, L. B. New J. Chem. 2022, 46, 4470.
[49]
Zhou, T.; Liu, R.; Wang, X.; Rui, M.; Zhao, X.; Lu, K. Asian J. Org. Chem. 2022, 11, e202200154.
[50]
Chen, S.; Yan, Q.; Fan, J.; Guo, C.; Li, L.; Liu, Z. Q.; Li, Z. Green Chem. 2023, 25, 153.
[51]
Yang, W. C.; Sun, Y.; Shen, L. Y.; Xie, X.; Yu, B. Mol. Catal. 2023, 535, 112819.
[52]
Ding, Q.; Zhou, X.; Fan, R. Org. Biomol. Chem. 2014, 12, 4807.
[53]
Zhu, M.; Zhou, K.; Zhang, X.; You, S. L. Org. Lett. 2018, 20, 4379.
[54]
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. K.; Unsworth, W. P. Chem. Sci. 2020, 11, 1353.
[55]
Gu, X.; Wei, Y.; Shi, M. Org. Chem. Front. 2021, 8, 6823.
[56]
Luo, X. K.; Cai, J.; Yin, Z. Y.; Luo, P.; Li, C. J.; Ma, H.; Seeram, N. P.; Gu, Q.; Xu, J. Org. Lett. 2018, 20, 991.
[57]
Hoxha, S.; Kalaitzakis, D.; Bosveli, A.; Montagnon, T.; Vassilikogiannakis, G. Org. Lett. 2021, 23, 5354.
[58]
Xie, X.; Wang, L.; Zhou, Q.; Ma, Y.; Wang, Z. M.; Li, P. Chin. Chem. Lett. 2022, 33, 5069.
[59]
Griffiths, O. M.; Ley, S. V. J. Org. Chem. 2022, 87, 13204.
[60]
Elinson, M. N.; Ilovaisky, A. I.; Merkulova, V. M.; Demchuk, D. V.; Belyakov, P. A.; Ogibin, Y. N.; Nikishin, G. I. Electrochim. Acta 2008, 53, 8346.
[61]
Wang, Z. H.; Ma, C.; Fang, P.; Xu, H. C.; Mei, T. S. Acta Chim. Sinica 2022, 80, 1115 (in Chinese).
[61]
(王振华, 马聪, 方萍, 徐海超, 梅天胜, 化学学报, 2022, 80, 1115.)
[62]
Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100.
[63]
Yang, D. S.; Li, G. Q.; Xing, C. Y.; Cui, W. W.; Li, K. X.; Wei, W. Org. Chem. Front. 2018, 5, 2974.
[64]
Wang, X.; Zhang, Y.; Sun, K.; Meng, J. P.; Zhang, B. Chin. J. Org. Chem. 2021, 41, 4588 (in Chinese).
[64]
(王薪, 张艳, 孙凯, 孟建萍, 张冰, 有机化学, 2021, 41, 4588.)
[65]
Hua, J.; Fang, Z.; Bian, M.; Ma, T.; Yang, M.; Xu, J., Liu, C. K.; He, W.; Zhu, N.; Yang, Z.; Guo, K. ChemSusChem 2020, 13, 2053.
[66]
Yu, K.; Kong, X.; Yang, J.; Li, G.; Xu, B.; Chen, Q. J. Org. Chem. 2020, 86, 917.
[67]
Chen, Z.; Tang, W.; Yang, S.; Yang, L. Green Synth. Catal. 2022, DOI: 10.1016/j.gresc.2022.09.006.
[68]
Zhang, Y.; Ma, C.; Struwe, J.; Feng, J.; Zhu, G.; Ackermann, L. Chem. Sci. 2021, 12, 10092.
[69]
Yang, W. C.; Zhang, M. M.; Sun, Y.; Chen, C. Y.; Wang, L. Org. Lett. 2021, 23, 6691.
[70]
Raji Reddy, C.; Kolgave, D. H. J. Org. Chem. 2021, 86, 17071.
Options
Outlines

/

〈 〉