Tandem michael addition-ring transformation reactions of 3-hydroxyoxindoles/3-aminooxindoles with olefinic azlactones: Direct access to structurally diverse spirocyclic oxindoles

Journal of Organic Chemistry

Volumn 79, Issue 11, 2014, Pages 5305-5314

  Cui, Bao Dong ^a,c   Zuo, Jian ^a,c   Zhao, Jian Qiang ^a,c   Zhou, Ming Qiang ^a,c   Wu, Zhi Jun ^b   Zhang, Xiao Mei ^a   Yuan, Wei Cheng ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

AZLACTONES; DIASTEREOSELECTIVITIES; HETEROATOMS; HIGH YIELD; OXINDOLES; STEREOCENTERS; TRANSFORMATION PROCESS; TRANSFORMATION REACTIONS;

ADDITION REACTIONS;

3 AMINOOXINDOLE; 3 HYDROXYOXINDOLE; ALKENE; INDOLE DERIVATIVE; LACTONE DERIVATIVE; NITROGEN; OXINDOLE; OXYGEN; SPIROCYCLIC OXINDOLE; UNCLASSIFIED DRUG; CYCLOALKANE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; CYCLOPARAFFINS; INDOLES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84902106473     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500432c     Document Type: Article

References (60)

1. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36
2. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
3. Badillo, J. J.; Hanhan, N. V.; Franz, A. K. Curr. Opin. Drug Discovery Dev. 2010, 13, 758
4. Rottmann, M.; McNamara, C.; Yeung, B. K. S.; Lee, M. C. S.; Zou, B.; Russell, B.; Seitz, P.; Plouffe, D. M.; Dharia, N. V.; Tan, J.; Cohen, S. B.; Spencer, K. R.; Gonzalez-Paez, G. E.; Lakshminarayana, S. B.; Goh, A.; Suwanarusk, R.; Jegla, T.; Schmitt, E. K.; Beck, H. P.; Brun, R.; Nosten, F.; Renia, L.; Dartois, V.; Keller, T. H.; Fidock, D. A.; Winzeler, E. A.; Diagana, T. T. Science 2010, 329, 1175
5. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104
6. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20
7. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
8. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
9. Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
10. Alba, A.-N. R.; Rios, R. Chem. - Asian J. 2011, 6, 720
11. Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K. Org. Biomol. Chem. 2012, 10, 5165
12. Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247
13. Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023
14. Ochi, M.; Kawasaki, K.; Kataoka, H.; Uchio, Y.; Nishi, H. Biochem. Biophys. Res. Commun. 2001, 283, 1118
15. Bernard, K.; Bogliolo, S.; Ehrenfeld, J. Br. J. Pharmacol. 2005, 144, 1037
16. Czarna, A.; Beck, B.; Srivastava, S.; Popowicz, G. M.; Wolf, S.; Huang, Y.; Bista, M.; Holak, T. A.; Dömling, A. Angew. Chem., Int. Ed. 2010, 49, 5352
17. Vintonyak, V. V.; Warburg, K.; Kruse, H.; Grimme, S.; Hübel, K.; Rauh, D.; Waldmann, H. Angew. Chem., Int. Ed. 2010, 49, 5902
18. Crosignani, S.; Jorand-Lebrun, C.; Page, P.; Campbell, G.; Colovray, V.; Missotten, M.; Humbert, Y.; Cleva, C.; Arrighi, J.-F.; Gaudet, M.; Johnson, Z.; Ferro, P.; Chollet, A. ACS Med. Chem. Lett. 2011, 2, 644
19. Heindel, N. D.; Minatelli, J. A. J. Pharm. Sci. 1981, 70, 84
20. Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod. 1999, 62, 569
21. Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328
22. Franz, A. K.; Dreyfuss, P. D.; Schreiber, S. L. J. Am. Chem. Soc. 2007, 129, 1020
23. Quasdorf, K. W.; Huters, A. D.; Lodewyk, M. W.; Tantillo, D. J.; Garg, N. K. J. Am. Chem. Soc. 2012, 134, 1396
24. Rana, S.; Natarajan, A. Org. Biomol. Chem. 2013, 11, 244
25. Yan, W.; Wang, D.; Feng, J.; Li, P.; Zhao, D.; Wang, R. Org. Lett. 2009, 11, 3874
26. Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255
27. Jung, H. H.; Buesking, A. W.; Ellman, J. A. Org. Lett. 2011, 13, 3912
28. Shen, K.; Liu, X.; Wang, G.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2011, 50, 4684
29. Bergonzini, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 971
30. Trost, B. M.; Hirano, K. Org. Lett. 2012, 14, 2446
31. Retini, M.; Bergonzini, G.; Melchiorre, P. Chem. Commun. 2012, 48, 3336
32. Chen, D.; Xu, M.-H. Chem. Commun. 2013, 49, 1327
33. Yamaguchi, E.; Mowat, J.; Luong, T.; Krische, M. J. Angew. Chem., Int. Ed. 2013, 52, 8428
34. Wang, Q.-L.; Peng, L.; Wang, F.-Y.; Zhang, M.-L.; Jia, L.-N.; Tian, F.; Xu, X.-Y.; Wang, L.-X. Chem. Commun. 2013, 49, 9422
35. Silvi, M.; Chatterjee, I.; Liu, Y.; Melchiorre, P. Angew. Chem., Int. Ed. 2013, 52, 10780
36. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426
37. Elford, T. G.; Hall, D. G. Synthesis 2010, 893
38. Cui, B.-D.; Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2013, 78, 8833
39. Shi, F.; Dai, A.-X.; Zhang, S.; Zhang, X.-H.; Tu, S.-J. Eur. J. Med. Chem. 2003, 38, 597
40. Yadav, L. D. S.; Singh, A. Tetrahedron Lett. 2003, 44, 5637
41. Tu, S.; Zhang, J.; Jia, R.; Jiang, B.; Zhang, Y.; Jiang, H. Org. Biomol. Chem. 2007, 5, 1450
42. Yadav, L. D. S.; Rai, V. K. Tetrahedron 2007, 63, 6924
43. Jiang, H.; Gschwend, B.; Albrecht, A.; Hansen, S. G.; Jørgensen, K. A. Chem. - Eur. J. 2011, 17, 9032
44. Alba, A.-N. R.; Calbet, T.; Font-Bardía, M.; Moyano, A.; Rios, R. Eur. J. Org. Chem. 2011, 2053
45. Steurer, M.; Jensen, K. L.; Worgull, D.; Jørgensen, K. A. Chem. - Eur. J. 2012, 18, 76
46. Halskov, K. S.; Johansen, T. K.; Davis, R. L.; Steurer, M.; Jensen, F.; Jørgensen, K. A. J. Am. Chem. Soc. 2012, 134, 12943
47. Uraguchi, D.; Ueki, Y.; Sugiyama, A.; Ooi, T. Chem. Sci. 2013, 4, 1308
48. DellAmico, L.; Albrecht, A.; Naicker, T.; Poulsen, P. H.; Jørgensen, K. A. J. Am. Chem. Soc. 2013, 135, 8063
49. Chen, W.-B.; Wu, Z.-J.; Pei, Q.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 3132
50. Chen, W.-B.; Wu, Z.-J.; Hu, J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2011, 13, 2472
51. Han, Y.-Y.; Chen, W.-B.; Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2012, 14, 490
52. Han, Y.-Y.; Han, W.-Y.; Hou, X.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2012, 14, 4054
53. Liu, X.-L.; Han, W.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2013, 15, 1246
54. Chen, W.-B.; Han, W.-Y.; Han, Y.-Y.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2013, 69, 5281
55. Han, W.-Y.; Li, S.-W.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Chem. - Eur. J. 2013, 19, 5551
56. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
57. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
58. Westermann, B.; Ayaz, M.; van Berkel, S. S. Angew. Chem., Int. Ed. 2010, 49, 846
59. Moyano, A.; Rios, R. Chem. Rev. 2011, 111, 4703
60. Pellissier, H. Chem. Rev. 2013, 113, 442