Proline-Catalyzed Diastereoselective Synthesis of Dihydroquinolinyl-Spirooxindole via Aza-Michael/Aldol Reaction

Abstract

An efficient diastereoselective synthesis of 1′,4′-dihydro-2′H-spiro[indoline-3,3′-quinolin]-2-one derivatives was achieved using catalytic amount of l-proline. The key reactions involved in the present tandem reaction are aza-Michael addition and aldol reaction. This atom economic reaction proceeded under mild conditions with a broad substrate scope and excellent diastereoselectivity in good to excellent yields.

Key words

l-Proline - organocatalytic reaction - spirooxindole - aza-Michael­ addition - aldol condensation

Publikationsverlauf

Eingereicht: 19. April 2023

Angenommen nach Revision: 22. Juni 2023

Accepted Manuscript online:
22. Juni 2023

Artikel online veröffentlicht:
18. Juli 2023

• References

• 1a Zhou L.-M, Qu R.-Y, Yang G.-F. Expert Opin. Drug Discov. 2020;  15:  603
• 1b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
• 2a Panda SS, Girgis AS, Aziz MN, Bekheit MS. Molecules 2023; 28: 618
• 2b Panda SS, Jones R RA, Bachawala P, Mohapatra PP. Mini Rev. Med. Chem. 2017; 17: 1515
• 2c Ye N, Chen H, Wold EA, Shi P.-Y, Zhou J. ACS Infect. Dis. 2016; 2: 382
• 2d Yu B, Yu D.-Q, Liu H.-M. Eur. J. Med. Chem. 2015; 97: 673
• 2e Zheng Y.-J, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673

Selected reviews on spiroxindole:
• 3a Nasri S, Bayat M, Mirzaei F. Top. Curr. Chem. 2021; 379: 25
• 3b Saranya PV, Neetha M, Aneeja T, Anilkumar G. RSC Adv. 2021; 11: 7146
• 3c Yan L.-J, Wang Y.-C. ChemistrySelect 2016; 1: 6948
• 3d Honga L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
• 3e Rios R. Chem. Soc. Rev. 2012; 41: 1060
• 3f Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165

Selected references for spiroxindole with six-membered rings:
• 4a Yang Y, Zhu B, Zhu L, Jiang Y, Guo C.-L, Gu J, Ouyang Q, Du W, Chen Y.-C. Chem. Sci. 2021; 12: 11399
• 4b Xu J, Song Y, He J, Dong S, Lin L, Feng X. Angew. Chem. Int. Ed. 2021; 60: 14521
• 4c Zhao K, Zhi Y, Shu T, Valkonen A, Rissanen K, Enders D. Angew. Chem. Int. Ed. 2016; 55: 12104
• 4d Huang Y, Zheng C, Chai Z, Zhaoa G. Adv. Synth. Catal. 2014; 356: 579
• 4e Li Y, Chen H, Shi C, Shi D, Ji S. J. Comb. Chem. 2010; 12: 231

Selected references for spiroxindole with five-membered rings:
• 5a Yang Y, Jiang Y, Du W, Chen Y.-C. Chem. Eur. J. 2020; 26: 1754
• 5b Yang Yi Y, Hua Y.-Z, Lu H.-J, Liu L.-T, Wang M.-C. Org. Lett. 2020; 22: 2527
• 5c Ramu G, Ambala S, Nanubolu JB, Babu BN. RSC Adv. 2019; 9: 35068
• 5d Gong Y, Wang G.-L, Wei Q.-D, Chen L, Liu X.-L, Tian M.-Y, Yang J, Feng T.-T, Zhou Y. Synth. Commun. 2018; 48: 1016
• 5e Yang Q.-Q, Xiao W, Du W, Ouyang Q, Chen Y.-C. Chem. Commun. 2018; 54: 1129
• 5f Laevens BA, Tao J, Murphy GK. J. Org. Chem. 2017; 82: 11903
• 5g Zhou Z, Wang Z.-X, Zhou Y.-C, Xiao W, Ouyang Q, Du W, Chen Y.-C. Nat. Chem. 2017; 9: 590
• 5h Xie Y, Que Y, Li T, Zhu L, Yua C, Yao C. Org. Biomol. Chem. 2015; 13: 1829
• 5i Suman K, Srinu L, Thennarasu T. Org. Lett. 2014; 16: 3732
• 5j Cao Y.-M, Shen F.-F, Zhang F.-T, Wang R. Chem. Eur. J. 2013; 19: 1184
• 5k Cao Y, Jiang X, Liu L, Shen F, Zhang F, Wang R. Angew. Chem. Int. Ed. 2011; 50: 9124
• 6 Xu S, Li C, Jia X, Li J. J. Org. Chem. 2014; 79: 11161
• 7 Zhu L, Chen Q, Shen D, Zhang W, Shen C, Zeng X, Zhong G. Org. Lett. 2016; 18: 2387
• 8 Shi F, Xing G.-J, Zhu R.-Y, Tan W, Tu S. Org. Lett. 2013; 15: 128
• 9 Xie Y, Que Y, Li T, Zhu L, Yu C, Yao C. Org. Biomol. Chem. 2015; 13: 1829
• 10 Huang X, Pham K, Yi W, Zhang X, Clamens C, Hyatt JH, Jasinsk JP, Tayvah U, Zhang W. Adv. Synth. Catal. 2015; 357: 3820
• 11 Sun Z, Tian S, Li S, Liu Y, Zhang Y, Li Y. Tetrahedron Lett. 2017; 58: 3401
• 12 Wang J, Zhao L, Zhao L, Pan X, Lv C, Zhi Y, Wang A, Zhao K, Hu L. Adv. Synth. Catal. 2020; 362: 2755
• 13a CCDC 2210439 (3d) and 2210415 (3i) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
• 13b See also the Supporting Information for the details of crystal structure.