Research Progress on the Synthetic Method of Five-Membered Spirooxindole Derivatives at C-3 Position

doi:10.6023/cjoc202104008

Abstract

As the core skeleton structure of many drugs and natural products, spirooxindole derivatives have a wide range of applications in the field of biology and medicine. Efficient synthesis of spirooxindole derivatives with high enantioselectivity and diastereoselectivity has gained much attention in organic chemical community. In this paper, the asymmetric synthetic methods for C-3 five-membered spirooxindoles by catalytic intramolecular reactions, intermolecular reactions and three- component reactions are reviewed. The future development direction of this field is also prospected.

Key words: spirooxindoles, synthetic method, asymmetric synthesis

Cite this article

Yitong Liu, Xiyuan Zhang, Zhiwei Miao. Research Progress on the Synthetic Method of Five-Membered Spirooxindole Derivatives at C-3 Position[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3965-3982.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 38

Figure 1. Bioactive molecule with a core structure of five- member-ring fused spirooxindoles

Scheme 1. Synthesis of spirooxindole via intramolecular nucleophilic reaction

Scheme 2. Synthesis of spirooxindole via intramolecular Friedel-Crafts reaction

Scheme 3. Synthesis of spirooxindole via intramolecular electrocyclization reaction

Scheme 4. Synthesis of spirooxindole by oxidation of tetrahydro-β-carboline

Scheme 5. Mechanism for oxidation synthesis of spirooxindole

Scheme 6. Oxidation/internal esterification of indole derivative catalyzed by NaI/H2O2

Scheme 7. Synthesis of spirooxindole catalyzed by micellar oxidant

Scheme 8. Asymmetric synthesis of spirooxindole from furan derivatives catalyzed by palladium catalyst

Scheme 9. Mechanism for synthesis of spirooxindole catalyzed by palladium catalyst

Scheme 10. Selective synthesis of Z/E configuration spirooxindole

Scheme 11. Mechanism for synthesis of Z/E configuration spirooxindole

Scheme 12. Synthesis of spirooxindole by N-(2-iodophenyl) amide catalyzed by iridium

Scheme 13. Mechanism for synthesis of spirooxindole over iridium catalyst

Scheme 14. Synthesis of spirooxindole by N-(2-trifluoromethesulfonatephenyl) amide catalyzed by Pd

Scheme 15. Synthesis of spirooxindole with a five- or six-member-ring produced by allene and ketone imide

Scheme 16. Mechanism for synthesis of five-member-ring spirooxindole from allene and ketone imide

Scheme 17. Reaction between allene and oxindole derivative to construct spirooxindole

Scheme 18. Mechanism for reaction between allene and oxindole derivatives

Scheme 19. [3+2] annulation between oxindole derivative and MBH phosphate ester

Scheme 20. Mechanism for reaction between oxindole derivative and MBH phosphate ester to construct spirooxindole

Scheme 21. Synthesis of spirooxindole by oxindole derivative and alkyne

Scheme 22. Mechanism for synthesis of spirooxindole catalyzed by phosphine

Scheme 23. Synthesis of spirooxindole catalyzed by chiral amine

Scheme 24. [3+2] annulation between bifundational oxindole and α,β-unsaturated aldehyde

Scheme 25. [4+1] annulation to construct spirooxindole catalyzed by Nickel

Scheme 26. Mechanism for synthesis of five-member-ring spirooxindole catalyzed by Ni

Scheme 27. [3+2] annulation to construct five-member-ring spirooxindole catalyzed by Ni

Scheme 28. Reaction between isatin, propanedioic acid and dimethyl acetylenedicarboxylate to construct spirooxindole

Scheme 29. Mechanism for three components cycloaddition to synthetize spirooxindole

Scheme 30. Synthesis of five-member-ring spirooxindole with pregnenolone

Scheme 31. Three component 1,3-dipolar cycloaddition catalyzed by chiral phosphoric acid

Scheme 32. Reaction between oxindole and o-phthalaldehyde to construct spirooxindole

Scheme 33. Mechanism for reaction between oxindole and o-phthalaldehyde

Scheme 34. Multi-component reaction to synthetize spirooxindole catalyzed by chiral amine

Scheme 35. [3+2] Cycloaddition catalyzed by chiral Cu complex

Scheme 36. Reaction between isatin derivatives, malononitrile and α-hydroxylketones to synthesize spirooxindoles

Scheme 37. Mechanism for reaction between isatin derivatives, malononitrile and α-hydroxylketones to synthesize spirooxindoles

References 38

[1]	Mei, G.-J.; Shi, F. Chem. Commun. 2018, 54, 6607. doi: 10.1039/C8CC02364F
[2]	Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651. doi: 10.1016/0040-4020(96)00737-5
[3]	Cui, C.-B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832. pmid: 8823522
[4]	Watson, A. F.; Liu, J.-F.; Bennaceur, K.; Drummond, C. J.; Endicott, J. A.; Golding, B. T.; Griffin, R. J.; Haggerty, K.; Lu, X.-H.; McDonnell, J. M.; Newell, D. R.; Noble, M. E. M.; Revill, C. H.; Riedinger, C.; Xu, Q.; Zhao, Y.; Lunec, J.; Hardcastle, L. R. Bioorg. Med. Chem. Lett. 2011, 21, 5916. doi: 10.1016/j.bmcl.2011.07.084 pmid: 21875801
[5]	Zhou, J.-Y.; Zhou, S.-W. J. Ethnopharmacol. 2010, 132, 15. doi: 10.1016/j.jep.2010.08.041
[6]	Xiao, Y.-L.; Zhou, Y.; Wang, J.; Wang, J.-X.; Liu, H. Chin. J. Org. Chem. 2015, 35, 2035. (in Chinese) doi: 10.6023/cjoc201504045
	(肖永龙, 周宇, 王江, 王进欣, 柳红, 有机化学, 2015, 35, 2035.) doi: 10.6023/cjoc201504045
[7]	Ohmatsu, K.; Ando, Y.; Nakashima, T.; Ooi, T. Chem 2016, 1, 802. doi: 10.1016/j.chempr.2016.10.012
[8]	Yin, B.-L.; Lai, J.-Q.; Zhang, Z.-R.; Jiang, H.-F. Adv. Synth. Catal. 2011, 353, 1961. doi: 10.1002/adsc.v353.11/12
[9]	Yin, B.-L.; Huang, L.; Zhang, X.-Y.; Ji, F.-H.; Jiang, H.-F. J. Org. Chem. 2012, 77, 6365. doi: 10.1021/jo301039y
[10]	Yin, B.-L.; Huang, L.; Wang, X.-J.; Liu, J.-C.; Jiang, H.-F. Adv. Synth. Catal. 2013, 355, 370.
[11]	Yin, X.-P.; Zeng, X.-P.; Liu, Y.-L.; Liao, F.-M.; Yu, J.-S.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 13740. doi: 10.1002/anie.201407677
[12]	Nakagawa, M.; Matsuki, K.; Hasegawa, K.; Hino, T. J. Chem. Soc., Chem. Commun. 1982, 742.
[13]	Xu, J.; Liang, L.-X.; Zheng, H.-H.; Chi, Y.-R.; Tong, R.-B. Nat. Commun. 2019, 10, 4754. doi: 10.1038/s41467-019-12768-4
[14]	Li, G.-F.; Huang, L.-W.; Xu, J.-C.; Sun, W.-S.; Xie, J.-Q.; Hong, L.; Wang, R. Adv. Synth. Catal. 2016, 358, 2873. doi: 10.1002/adsc.201600441
[15]	Wang, D.-G.; Lu, X.-B.; Sun, S.-H.; Yu, H.-B.; Su, H.-M.; Wu, Y.-Z.; Zhong, F.-R. Eur. J. Org. Chem. 2019, 6028.
[16]	Liu, J.-C.; Peng, H.; Lu, L.; Xu, X.-B.; Jiang, H.-F.; Yin, B.-L. Org. Lett. 2016, 18, 6440. doi: 10.1021/acs.orglett.6b03339
[17]	Liu, J.-C.; Xu, X.-B.; Li, J.-Y.; Liu, B.; Jiang, H.-F.; Yin, B.-L. Chem. Commun. 2016, 52, 9550. doi: 10.1039/C6CC04298H
[18]	Liu, J.-C.; Peng, H.; Yang, Y.-J.; Jiang, H.-F.; Yin, B.-L. J. Org. Chem. 2016, 81, 9695. doi: 10.1021/acs.joc.6b01774
[19]	Chen, J.-Q.; Wei, Y.-L.; Xu, G.-Q.; Liang, Y.-M.; Xu, P.-F. Chem. Commun. 2016, 52, 6455. doi: 10.1039/C6CC02007K
[20]	Ratushnyy, M.; Kvasovs, N.; Sarkar, S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2020, 59, 10316. doi: 10.1002/anie.v59.26
[21]	Ying, A.-G.; Wu, C.-L.; Fu, Y.-Q.; Ren, S.-B.; Liang, H.-D. Chin. J. Org. Chem. 2012, 32, 1587. (in Chinese) doi: 10.6023/cjoc201203009
	(应安国, 武承林, 付永前, 任世斌, 梁华定, 有机化学, 2012, 32, 1587.) doi: 10.6023/cjoc201203009
[22]	Sankar, M. G.; Castro, M. G.; Golz, C.; Strohmann, C.; Kumar, K.; Ihsar, M. P. S. Angew. Chem., Int. Ed. 2016, 55, 9709. doi: 10.1002/anie.201603936
[23]	Feng, J.-X.; Huang, Y. Chem. Commun. 2019, 55, 14011. doi: 10.1039/C9CC07346A
[24]	Yu, C.-B.; Zheng, W.-P.; Zhan, J.-C.; Sun, Y.-C.; Miao, Z.-W. RSC Adv. 2014, 4, 63246. doi: 10.1039/C4RA12997K
[25]	Zhang, J.-Y.; Cheng, C.; Wang, D.; Miao, Z.-W. J. Org. Chem. 2017, 82, 10121. doi: 10.1021/acs.joc.7b01582
[26]	Lin, Y.; Du, D.-M. Chin. J. Org. Chem. 2020, 40, 3214. (in Chinese) doi: 10.6023/cjoc202005065
	(林晔, 杜大明, 有机化学, 2020, 40, 3214.) doi: 10.6023/cjoc202005065
[27]	Duan, S.-W.; Li, Y.; Liu, Y.-Y.; Zou, Y.-Q.; Shi, D.-Q.; Xiao, W.-J. Chem. Commun. 2012, 48, 5160. doi: 10.1039/c2cc30931a
[28]	Ding, L.-Z.; Zhong, T.-S.; Wu, H.; Wang, Y.-M. Eur. J. Org. Chem. 2014, 5139.
[29]	Buxton, C. S.; Blakemore, D. C.; Bower, J. F. Angew. Chem., Int. Ed. 2017, 56, 13824. doi: 10.1002/anie.201707531
[30]	Zhou, P.-F.; Cai, Y.-F.; Lin, L.-L.; Lian, X.-J.; Xia, Y.; Liu, X.-H.; Feng, X.-M. Adv. Synth. Catal. 2015, 357, 695. doi: 10.1002/adsc.v357.4
[31]	Tan, W.; Zhu, X.-T.; Zhang, S.; Xing, G.-J.; Zhu, R.-Y.; Shi, F. RSC Adv. 2013, 3, 10875. doi: 10.1039/c3ra40874d
[32]	Yu, B.; Sun, X.-N. Shi, X.-J.; Qi, P.-P.; Zheng, Y.-C.; Yu, D.-Q.; Liu, H.-M. Steroids 2015, 102, 92. doi: 10.1016/j.steroids.2015.08.003
[33]	Shi, F.; Tao, Z.-L.; Luo, S.-W.; Tu, S.-J.; Gong, L.-Z. Chem.-Eur. J. 2012, 18, 6885. doi: 10.1002/chem.201200358
[34]	Guo, C.; Song, J.; Gong, L.-Z. Org. Lett. 2013, 15, 2676. doi: 10.1021/ol400983j
[35]	Yang, J.; Liu, X.-W.; Wang, D.-D.; Tian, M.-Y.; Han, S.-N.; Feng, T.-T.; Liu, X.-L.; Mei, R.-Q.; Zhou, Y. Tetrahedron 2016, 72, 8523. doi: 10.1016/j.tet.2016.10.050
[36]	Wu, M.-Y.; He, W.-W.; Liu, X.-Y.; Tan, B. Angew. Chem., Int. Ed. 2015, 54, 9409. doi: 10.1002/anie.201504640
[37]	Salahi, F.; Taghizadeh, M. J.; Arvinnezhad, H.; Moemeni, M.; Jadidi, K.; Notas, B. Tetrahedron Lett. 2014, 55, 1515. doi: 10.1016/j.tetlet.2013.11.097
[38]	Miao, Y.-H.; Hua, Y.-Z.; Wang, M.-C. Org. Biomol. Chem. 2019, 17, 7172. doi: 10.1039/C9OB01233H

C-3位五元螺环吲哚酮衍生物合成方法研究进展