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

doi:10.6023/cjoc202304014

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 26

Scheme 1. Visible-light-induced construction of 2-azaspiro- [4.5]decane from α-bromo-N-benzylalkylamine

Scheme 2. Construction of spiropyrrolines by photoredox of phenol derivatives containing ketoxime structure

Scheme 3. Visible-light-induced construction of spirolides from biaryl compounds

Scheme 4. Construction of spironocyclohexadiene compounds by photoredox of halogenated aromatic hydrocarbons

Scheme 5. Construction of spiral ring compounds by photoredox aromatic carboxylic acids

Scheme 6. Photocatalytic construction of azaspiro[4.5]deca-6,9- diene-3,8-dione from N-benzylpropionamide

Scheme 7. Visible-light-induced construction of 3-sulfonyl- azaspiro[4.5]trienone from alkenes

Scheme 8. Visible-light-induced construction of carbospirocyclic compounds from 2-bromo-1,3-dicarbonyl compounds

Scheme 9. Visible-light-induced synthesis of sulfonated spiro[4.5]trienone from propionamide, aniline and sulfur dioxide

Scheme 10. Visible-light-induced construction of 3-thiazaspiro- [4.5]trienone from acrylamide and thiophene compounds

Scheme 11. Visible-light-induced construction of halospiro- [4.5]trienones from N-arylpropionamides

Scheme 12. Visible-light-induced construction of 3-difluoro- methylspirone[4.5]trienone from N-arylpropionamides

Scheme 13. Visible-light-induced construction of spiro[5.5]- trienone from biaryl compounds

Scheme 14. Visible-light-induced construction of spiro[5.5]- trienone from aryl alkynone

Scheme 15. Visible-light-induced construction of spiroindolines from indole derivatives

Scheme 16. Visible-light-induced construction of spiro-indoles by indole-based alkynones

Scheme 17. Visible-light-induced construction of multi-substituted spiro[2.3] ring skeletons from methylenecyclopropane

Scheme 18. Visible-light-induced one-pot conversion of furan to 1-azacyclic alkaloid skeleton

Scheme 19. Visible-light-induced construction of spiro-bridged compounds through cyclization

Scheme 20. Visible-light-induced N-allylsulfonamide and construction β-helical cyclopyrrolidine from olefin

Scheme 21. Electrochemically induced cyclization of aryl spirocyclization to construct spiro[4.5]trienone

Scheme 22. Electrocatalytic synthesis of spiro[4.5]trienone by halogenation of N-arylalkylamides

Scheme 23. Electrocatalytic synthesis of 3-halogenated spiro[4.5]trienones from aryl derivatives

Scheme 24. Electrocatalytic synthesis of sifluoro/trifluoro- methylated spiro[5.5]trienones from biaryl compounds

Scheme 25. Electrocatalytic construction of spiro[5.5]trienone from AgSCF3

Scheme 26. Electrocatalytic synthesis of selenide diphenylcycloheptone/spiro[5.5]trienone from biaryl compounds

References 70

[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).
	(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. doi: 10.1016/j.molstruc.2017.09.086
[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. doi: 10.1021/acs.jmedchem.0c00829
[17]	Hiesinger, K.; Dar’in, D.; Proschak, E.; Krasavin, M. J. Med. Chem. 2020, 64, 150. doi: 10.1021/acs.jmedchem.0c01473
[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. doi: 10.1021/jacs.0c03926
[24]	Zhou, C.; Shatskiy, A.; Temerdashev, A. Z.; Kärkäs, M. D.; Dinér, P. Chem. Commun. 2022, 5, 92. doi: 10.1038/s42004-022-00706-3
[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. doi: 10.1021/acs.joc.2c00579 pmid: 35678323
[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. doi: 10.1039/D3CC01102J
[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. doi: 10.1021/acs.orglett.2c01977
[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. doi: 10.1021/acscentsci.2c00204
[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. 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. doi: 10.1039/C7GC02330H
[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. doi: 10.1021/acs.orglett.8b02463
[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. doi: 10.1021/acs.joc.8b02881
[33]	Dong, W. H.; Yuan, Y.; Xie, X. M.; Zhang, Z. G. Org. Lett. 2020, 22, 528. doi: 10.1021/acs.orglett.9b04283
[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. doi: 10.1021/acs.joc.0c02477
[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. doi: 10.1021/acs.orglett.8b02463
[36]	Liu, Y.; Wang, Q. L.; Chen, Z.; Zhou, Q.; Xiong, B. Q.; Zhang, P. L.; Tang, K. W. Chem. Commun. 2019, 55, 12212. doi: 10.1039/C9CC05949K
[37]	Ouyang, X. H.; Song, R. J.; Li, Y.; Liu, B.; Li, J. H. J. Org. Chem. 2014, 79, 4582. doi: 10.1021/jo5005982
[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. doi: 10.1039/C4CC06923D
[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. doi: 10.1016/j.cclet.2019.06.008
[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. doi: 10.1002/ajoc.v10.3
[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. doi: 10.1039/D2NJ00131D
[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. doi: 10.1039/D2GC03710F
[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. doi: 10.1039/C4OB00371C
[53]	Zhu, M.; Zhou, K.; Zhang, X.; You, S. L. Org. Lett. 2018, 20, 4379. doi: 10.1021/acs.orglett.8b01899
[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. doi: 10.1039/C9SC05311E
[55]	Gu, X.; Wei, Y.; Shi, M. Org. Chem. Front. 2021, 8, 6823. doi: 10.1039/D1QO01373D
[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. doi: 10.1021/acs.orglett.7b03935
[57]	Hoxha, S.; Kalaitzakis, D.; Bosveli, A.; Montagnon, T.; Vassilikogiannakis, G. Org. Lett. 2021, 23, 5354. doi: 10.1021/acs.orglett.1c01661
[58]	Xie, X.; Wang, L.; Zhou, Q.; Ma, Y.; Wang, Z. M.; Li, P. Chin. Chem. Lett. 2022, 33, 5069. doi: 10.1016/j.cclet.2022.03.084
[59]	Griffiths, O. M.; Ley, S. V. J. Org. Chem. 2022, 87, 13204. doi: 10.1021/acs.joc.2c01684 pmid: 36103403
[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. doi: 10.1016/j.electacta.2008.06.044
[61]	Wang, Z. H.; Ma, C.; Fang, P.; Xu, H. C.; Mei, T. S. Acta Chim. Sinica 2022, 80, 1115 (in Chinese). doi: 10.6023/A22060260
	(王振华, 马聪, 方萍, 徐海超, 梅天胜, 化学学报, 2022, 80, 1115.) doi: 10.6023/A22060260
[62]	Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100. doi: 10.1039/D0QO00849D
[63]	Yang, D. S.; Li, G. Q.; Xing, C. Y.; Cui, W. W.; Li, K. X.; Wei, W. Org. Chem. Front. 2018, 5, 2974. doi: 10.1039/C8QO00899J
[64]	Wang, X.; Zhang, Y.; Sun, K.; Meng, J. P.; Zhang, B. Chin. J. Org. Chem. 2021, 41, 4588 (in Chinese).
	(王薪, 张艳, 孙凯, 孟建萍, 张冰, 有机化学, 2021, 41, 4588.) doi: 10.6023/cjoc202109046
[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. doi: 10.1002/cssc.v13.8
[66]	Yu, K.; Kong, X.; Yang, J.; Li, G.; Xu, B.; Chen, Q. J. Org. Chem. 2020, 86, 917. doi: 10.1021/acs.joc.0c02429
[67]	Chen, Z.; Tang, W.; Yang, S.; Yang, L. Green Synth. Catal. 2022, DOI: 10.1016/j.gresc.2022.09.006. 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. doi: 10.1039/d1sc02682h pmid: 34377402
[69]	Yang, W. C.; Zhang, M. M.; Sun, Y.; Chen, C. Y.; Wang, L. Org. Lett. 2021, 23, 6691. doi: 10.1021/acs.orglett.1c02260
[70]	Raji Reddy, C.; Kolgave, D. H. J. Org. Chem. 2021, 86, 17071. doi: 10.1021/acs.joc.1c02182

光/电化学驱动螺环化合物的合成研究进展