Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2020; 52(09): 1387-1397
DOI: 10.1055/s-0039-1691597
DOI: 10.1055/s-0039-1691597
paper
1,3-Dipolar Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and O-Vinylphosphonylated Salicylaldehydes for Diastereoselective Synthesis of Oxindole Spiro-P,N-polycyclic Heterocycles
We gratefully acknowledge the financial support from Program of Natural Science Foundation of Hainan Province (2019RC215) and Graduate Innovative Research Project of Hainan Normal University (Hsyx2018-25).Further Information
Publication History
Received: 04 November 2019
Accepted after revision: 21 January 2020
Publication Date:
12 February 2020 (online)
Abstract
An efficient stereoselective assembly strategy for the construction of pyrrolidin-2,3′-oxindole cis-fused phosphadihydrocoumarins was established. The process involves the condensation of O-vinylphosphonylated salicylaldehydes and 3-amino oxindoles followed by intermolecular cycloaddition with high diastereoselectivity and atom economy.
Key words
3-amino oxindole - azomethine ylide - dipolar cycloaddition - pyrrolidin-2,3′-oxindoles - cis-fused phosphadihydrocoumarins - O-vinylphosphonylated salicylaldehydeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691597.
- Supporting Information
-
References
- 1a Inoue M. Chem. Rev. 2005; 105: 4379
- 1b Ganem B. Acc. Chem. Res. 2009; 42: 463
- 1c Campos CA, Gianino JB, Ashfeld BL. Org. Lett. 2013; 15: 2656
- 1d Urabe D, Asaba T, Inoue M. Chem. Rev. 2015; 115: 9207
- 2a Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432
- 2b Kitahara K, Shimokawa J, Fukuyama T. Chem. Sci. 2014; 5: 904
- 2c Watanabe K. Jpn. J. Antibiot. 2015; 68: 55
- 2d Chen L, Xie J, Song H, Liu Y, Gu Y, Wang L, Wang Q. J. Agric. Food Chem. 2016; 64: 6508
- 2e Ma Y, Fan C, Jia B, Cheng P, Liu J, Ma Y, Qiao K. Chirality 2017; 29: 737
- 3a Kumar A, Gupta G, Bishnoi AK, Saxena R, Saini KS, Konwar R, Kumar S, Dwivedi A. Bioorg. Med. Chem. 2015; 23: 839
- 3b Yu B, Sun XN, Shi XJ, Qi PP, Zheng YC, Yu DQ, Liu HM. Steroids 2015; 102: 92
- 4a Bhaskar G, Arun Y, Balachandran C, Saikumar C, Perumal PT. Eur. J. Med. Chem. 2012; 51: 79
- 4b Singh SB, Tiwari K, Verma PK, Srivastava M, Tiwari KP, Singh J. Supramol. Chem. 2013; 25: 255
- 4c Kumar RS, Antonisamy P, Almansour AI, Arumugam N, Periyasami G, Altaf M, Kim H.-R, Kwon K.-B. Eur. J. Med. Chem. 2018; 152: 417
- 5a Gollner A, Rudolph D, Arnhof H, Bauer M, Blake SM, Boehmelt G, Cockroft XL, Dahmann G, Ettmayer P, Gerstberger T, Karolyi-Oezguer J, Kessler D, Kofink C, Ramharter J, Rinnenthal J, Savchenko A, Schnitzer R, Weinstabl H, Weyer-Czernilofsky U, Wunberg T, McConnell DB. J. Med. Chem. 2016; 59: 10147
- 5b Gao X, Wei M, Shan W, Liu Q, Gao J, Liu Y, Zhu S, Yao H. Pharmacol. Res. 2019; 148: 104400
- 6a Weber GF, Waxman DJ. Biochem. Pharmacol. 1993; 45: 1685
- 6b Palacios F, Alonso C, de los Santos JM. Chem. Rev. 2005; 105: 899
- 6c Stoianova DS, Whitehead A, Hanson PR. J. Org. Chem. 2005; 70: 5880
- 7a Borch RF, Canute GW. J. Med. Chem. 1991; 34: 3044
- 7b Clarion L, Jacquard C, Sainte-Catherine O, Loiseau S, Filippini D, Hirlemann M.-H, Volle J.-N, Virieux D, Lecouvey M, Pirat J.-L, Bakalara N. J. Med. Chem. 2012; 55: 2196
- 7c Dayde B, Pierra C, Gosselin G, Surleraux D, Ilagouma AT, Laborde C, Volle J.-N, Virieux D, Pirat J.-L. Eur. J. Org. Chem. 2014; 1333
- 8 Li X, Zhang D, Pang H, Shen F, Fu H, Jiang Y, Zhao Y. Org. Lett. 2005; 7: 4919
- 9 Li Z, Han J, Jiang Y, Browne P, Knox RJ, Hu L. Bioorg. Med. Chem. 2003; 11: 4171
- 10a Wilson EE, Rodriguez KX, Ashfeld BL. Tetrahedron 2015; 71: 5765
- 10b Zheng PF, Ouyang Q, Niu SL, Shuai L, Yuan Y, Jiang K, Liu TY, Chen YC. J. Am. Chem. Soc. 2015; 137: 9390
- 10c Tian YM, Tian LM, He X, Li CJ, Jia XS, Li J. Org. Lett. 2015; 17: 4874
- 10d Wang SZ, Jiang Y, Wu SC, Dong GQ, Miao ZY, Zhang WN, Sheng CQ. Org. Lett. 2016; 18: 1028
- 10e Zhu LY, Chen QL, Shen D, Zhang WH, Shen C, Zeng XF, Zhong GF. Org. Lett. 2016; 18: 2387
- 10f Zhao K, Zhi Y, Li XY, Puttreddy R, Rissanen K, Enders D. Chem. Commun. 2016; 52: 2249
- 10g Luo MP, Yuan RJ, Liu XS, Yu LQ, Wei WH. Chem. Eur. J. 2016; 22: 9797
- 10h Chaudhari PD, Hong BC, Lee GH. Org. Lett. 2017; 19: 6112
- 10i Jiang S, Guo HM, Yao S, Shi DQ, Xiao WJ. J. Org. Chem. 2017; 82: 10433
- 10j Jiang Y, Yu SW, Yang Y, Liu YL, Xu XY, Zhang XM, Yuan WC. Org. Biomol. Chem. 2018; 16: 6647
- 10k Yan J, Shi KX, Zhao CT, Ding LY, Jiang SS, Yang LM, Zhong GF. Chem. Commun. 2018; 54: 1567
- 10l Liu T, Feng JJ, Chen C, Deng ZJ, Kotagiri R, Zhou GX, Zhang XH, Cai Q. Org. Lett. 2019; 21: 4505
- 10m Qiu B, Xu DQ, Sun QS, Lin J, Sun W. Org. Lett. 2019; 21: 618
- 11a Sun H, Wang X, Chen Y, Ouyang L, Liu J, Zhang Y. Tetrahedron Lett. 2014; 55: 5434
- 11b Zhu G, Wang B, Bao X, Zhang H, Wei Q, Qu J. Chem. Commun. 2015; 51: 15510
- 12a Wei Q, Zhu G, Zhang H, Qu J, Wang B. Eur. J. Org. Chem. 2016; 5335
- 12b Cui B, Chen Y, Shan J, Qin L, Yuan C, Wang Y, Han W, Wan N, Chen Y. Org. Biomol. Chem. 2017; 15: 8518
- 12c Zhu G, Wei Q, Chen H, Zhang Y, Shen W, Qu J, Wang B. Org. Lett. 2017; 19: 1862
- 12d He J, Sun R.-G, Fan L, Tian S.-Y, Huang T.-P, Chen Z, Chen L. Synthesis 2019; 51: 1353
- 13 Zhu G, Wu S, Bao X, Cui L, Zhang Y, Qu J, Chen H, Wang B. Chem. Commun. 2017; 53: 4714
- 14 Wu S, Zhu G, Wei S, Chen H, Qu J, Wang B. Org. Biomol. Chem. 2018; 16: 807
- 15 Zhu G, Liu S, Wu S, Peng L, Qu J, Wang B. J. Org. Chem. 2017; 82: 4317
- 16 CCDC 1912906 contains 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/getstructures.