Iodine-catalyzed cascade formal [3 + 3] cycloaddition reaction of indolyl alcohol derivatives with enaminones: Constructions of functionalized spirodihydrocarbolines

ACS Catalysis

Volumn 3, Issue 11, 2013, Pages 2501-2504

  Hao, Wen Juan ^a   Wang, Shun Yi ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

carbolines; cascade reaction; formal 3 + 3 cycloaddition reaction; indolyl alcohol; iodine

Indexed keywords

ALCOHOL DERIVATIVES; CARBOLINES; CASCADE REACTIONS; CYCLOADDITION REACTION; ENAMINONES; FUNCTIONALIZED; PRACTICAL METHOD;

CATALYSIS; CYCLOADDITION;

IODINE;

EID: 84887349413     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs400703u     Document Type: Article

References (56)

1. Buckingham, J., Baggaley, K. H., Roberts, A. D., Szabo, L. F., Eds.; Dictionary of Alkaloids, 2 nd ed., CRC Press: Boca Raton, FL, 2010.
2. Ohmoto, T.; Koike, K. In The Alkaloids, Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, p 135.
3. Butler, K. V.; Kalin, J.; Brochier, C.; Vistoli, G.; Langley, B.; Kozikowski, A. P. J. Am. Chem. Soc. 2010, 132, 10842
4. Kalin, J. H.; Butler, K. V.; Akimova, T.; Hancock, W. W.; Kozikowski, A. P. J. Med. Chem. 2012, 55, 639
5. Gore, S.; Baskaran, S.; König, B. Org. Lett. 2012, 14, 4568
6. Zhang, L.; Meier, W.; Wats, E.; Costello, T. D.; Ma, P.; Ensinger, P. O.; Rodgers, J. M.; Jacobson, I. C.; Rajagopalan, P. Tetrahedron Lett. 1995, 36, 8387
7. Chen, J.; Dong, X.; Liu, T.; Lou, J.; Jiang, C.; Huang, W.; He, Q.; Yang, B.; Hu, Y. Bioorg. Med. Chem. 2009, 17, 3324
8. Chen, J.; Liu, T.; Wu, R.; Lou, J.; Cao, J.; Dong, X.; Yang, B.; He, Q.; Hu, Y. Bioorg. Med. Chem. 2010, 18, 8478
9. Ye, L.; Tian, Y.; Li, Z.; Zhang, J.; Wu, S. Helv. Chim. Acta 2012, 95, 320
10. Rajagopalan and Parthasarathi; WO1994003455, PCT/US1993/006823, 1994.
11. Sako, K.; Aoyama, H.; Sato, S.; Hashimoto, Y.; Baba, M. Bioorg. Med. Chem. 2008, 16, 3780
12. Ivachtchenko, A. V.; Frolov, E. B; Mitkin, O. D.; Kysil, V. M.; Khvat, A. V.; Okun, I. M.; Tkachenko, S. E. Bioorg. Med. Chem. Lett. 2009, 19, 3183
13. Gao, M.; Wang, M. Bioorg. Med. Chem. Lett. 2010, 20, 2529
14. Bharadwaj, P. R.; Verdile, G.; Barr, R. K.; Gupta, V.; Steele, J. W.; Lachenmayer, M. L.; Yue, Z.; Ehrlich, M. E.; Petsko, G.; Ju, S. J. Alzheimer's Dis. 2012, 32, 949
15. Fink, M.; Irwin, P. Psychopharmacology (Berlin) 1980, 72, 67
16. McEvoy, J. P.; Berney, S.; Wilson, W. H.; Ban, T. A.; Guy, W. Int. Pharmacopsychiatry 1980, 15, 318
17. Bridoux, A.; Pommery, J.; Pommery, N.; Henichart, J. P. Bioorg. Med. Chem. 2010, 18, 3910
18. Harbert, C. A.; Plattner, J. J.; Welch, W. M.; Weissman, A.; Koe, B. K. J. Med. Chem. 1980, 23, 635
19. Butler, K. V.; Kalin, J.; Brochier, C.; Vistoli, G.; Langley, B.; Kozikowski, A. P. J. Am. Chem. Soc. 2010, 132, 10842
20. Sheng, C.; Che, X.; Wang, W.; Wang, S.; Cao, Y.; Yao, J.; Zhang, W. Eur. J. Med. Chem. 2011, 46, 1706
21. Vecchietti, V.; Clarke, G. D.; Colle, R.; Giardina, G.; Petrone, G.; Sbacchi, M. J. Med. Chem. 1991, 34, 2624
22. Robaa, D.; Enzensperger, C.; Lehmann, J. J. Med. Chem. 2010, 53, 2646
23. Lee, Y.; Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2011, 13, 5564
24. Kudzma, L. V. Synthesis 2003, 11, 1661
25. Lv, J.; Li, J.; Zhang-Negrerie, D.; Shang, S.; Gao, Q.; Du, Y.; Zhao, K. Org. Biomol. Chem. 2013, 11, 1929
26. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006, p 672.
27. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137
28. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
29. Tietze, L. F. Chem. Rev. 1996, 96, 115
30. Pellissier, H. Tetrahedron 2006, 62, 1619
31. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992, p 502.
32. Trost, B. M. Science 1991, 254, 1471
33. Trost, B. M. Angew. Chem. 1995, 107, 285
34. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
35. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice: Oxford University Press: Oxford, 2000, p 135.
36. Matlack, A. S. Introduction to Green Chemistry; Marcel Dekker: New York, 2001, p 570.
37. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
38. Wang, S.-Y. Synlett 2004, 2642
39. Banerjee, A. K.; Vera, W.; Mora, H.; Laya, M. S.; Bedoya, L.; Cabrera, E. V. J. Sci. Ind. Res. India 2006, 65, 299
40. Zhang, Z.; Liu, Q. Prog. Chem. 2006, 18, 270
41. Shen, S.; Xu, X.; Ji, S. Chin. J. Org. Chem. 2009, 29, 806
42. Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 45, 979
43. Ren, Y.-M.; Cai, C.; Yang, R.-C. RSC Adv. 2013, 3, 7182
44. Song, J.; Guo, C.; Adele, A.; Yin, H.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 3319
45. Guo, C.; Song, J.; Huang, J.-Z.; Chen, P.-H.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 1046
46. Guo, Q.-X.; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620
47. Huang, J.; Luo, S.; Gong, L. Acta Chim. Sin. 2013, 71, 879
48. For a review, see: Palmieri, A.; Petrini, M.; Shaikh, R. R. Org. Biomol. Chem. 2010, 8, 1259
49. Han, X.; Li, H.; Hughes, R. P.; Wu, J. Angew. Chem., Int. Ed. 2012, 51, 10390
50. Xiao, Y.-C.; Zhou, Q.-Q.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2012, 14, 5940
51. Wang, L.; Xie, X.; Liu, Y.-H. Org. Lett. 2012, 14, 5848
52. Wang, S.-Y.; Ji, S.-J. Tetrahedron 2006, 62, 1527
53. Ji, S.-J.; Wang, S.-Y.; Zhang, Y.; Loh, T.-P. Tetrahedron 2004, 60, 2051
54. Zeng, X.-F.; Ji, S.-J.; Wang, S.-Y. Tetrahedron 2005, 61, 10235
55. Zhang, Y.; Wang, S.-Y.; Xu, X.-P.; Jiang, R.; Ji, S.-J. Org. Biomol. Chem. 2013, 11, 1933
56. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66