Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1540-1543

  Jiang, Bo ^a   Wang, Xue ^a   Xu, Hai Wei ^a   Tu, Man Su ^a   Tu, Shu Jiang ^a   Li, Guigen ^b,c  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

^c TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MICROWAVE RADIATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACRIDINES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MICROWAVES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84875940478     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400322v     Document Type: Article

References (48)

1. Melhado, A. D.; Brenzovitch, W. E.; Lackner, A. D.; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 8885-8887
2. Adams, G. L.; Carroll, P. J.; Smith, A. B., III. J. Am. Chem. Soc. 2013, 135, 519-528
3. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753
4. Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730-4756
5. Sutherland, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Elmsford, NY, 1991; Vol. 1, pp 341-377.
6. Gunawardana, G. P.; Koehn, F. E.; Lee, A. Y.; Clardy, J.; He, H. Y.; Faulkner, D. J. J. Org. Chem. 1992, 57, 1523-1526
7. Agrawal, M. S.; Bowden, B. F. Nat. Prod. Res. 2007, 21, 782-786
8. Le Bozec, L.; Moody, C. J. Aust. J. Chem. 2009, 62, 639-647
9. Inman, W. D.; O'Neill-Johnson, M.; Crews, P. J. Am. Chem. Soc. 1990, 112, 1-4
10. West, R. R.; Mayne, C. L.; Ireland, C. M.; Brinen, L. S.; Clardy, J. Tetrahedron Lett. 1990, 31, 3271-3274
11. Wang, H.; Li, L.; Lin, W.; Xu, P.; Huang, Z.; Shi, D. Org. Lett. 2012, 14, 4598-4601
12. Jiang, B.; Wang, X.; Li, M.-Y.; Wu, Q.; Ye, Q.; Xu, H.-W.; Tu, S.-J. Org. Biomol. Chem. 2012, 10, 8533-8538
13. Kefayati, H.; Narchin, F.; Rad-Moghadam, K. Tetrahedron Lett. 2012, 53, 4573-4575
14. Gellerman, G.; Rudi, A.; Kashman, Y. Tetrahedron 1994, 50, 12959
15. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
16. Tietze, L. F.; Brasche, G.; Gerike, K. Domino Reactions in Organic Chemistry; Wiley-VCH: Weinheim, 2006.
17. Padwa, A. Chem. Soc. Rev. 2009, 38, 3072-3081
18. Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367-378
19. Ganem, B. Acc. Chem. Res. 2009, 42, 463-472
20. Turner, C. I.; Williamson, R. M.; Tumer, P.; Sherburn, M. S. Chem. Commun. 2003, 1610-1611
21. Padwa, A.; Brodney, M. B.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735-3745
22. Stearman, C. J.; Wilson, M.; Padwa, A. J. Org. Chem. 2009, 74, 3491-3499
23. France, S.; Boonsombat, J.; Leverett, C. A.; Padwa, A. J. Org. Chem. 2008, 73, 8120-8123
24. Topczewski, J. J.; Callahan, M. P.; Neighbors, J. D.; Wiemer, D. F. J. Am. Chem. Soc. 2009, 131, 14630-14631
25. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509
26. Huang, A. X.; Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 9999-10003
27. Jiang, B.; Li, C.; Shi, F.; Tu, S.-J.; Kaur, P.; Wever, W.; Li, G. J. Org. Chem. 2010, 75, 2962-2965
28. Jiang, B.; Tu, S.-J.; Kaur, P.; Wever, W.; Li, G. J. Am. Chem. Soc. 2009, 131, 11660-11661
29. Jiang, B.; Wang, X.; Shi, F.; Tu, S.-J.; Ai, T.; Ballew, A.; Li, G. J. Org. Chem. 2009, 74, 9486-9489
30. Jiang, B.; Li, Q.-Y.; Zhang, H.; Tu, S.-J.; Pindi, S.; Li, G. Org. Lett. 2012, 14, 700-703
31. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753-1765
32. Yang, J. W.; Fonseca, M. T. H.; List, B. J. Am. Chem. Soc. 2005, 127, 15036-15037
33. Groundwaater, P. W.; Munawar, M. A. Adv. Heterocycl. Chem. 1998, 70, 88-161
34. Cookson, J. C.; Heald, R. A.; Stevens, M. F. G. J. Med. Chem. 2005, 48, 7198-7207
35. Antonini, I.; Polucci, P.; Magnano, A.; Sparapani, S.; Martelli, S. J. Med. Chem. 2004, 47, 5244-5250
36. Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755-3758
37. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287-8288
38. Nishina, Y.; Kida, T.; Ureshino, T. Org. Lett. 2011, 13, 3960-3963
39. Paquette, L. A. J. Org. Chem. 1964, 29, 3447-3449
40. Paquette, L. A.; Broadhurst, M. J. J. Org. Chem. 1973, 38, 1886-1893
41. Sato, E.; Ikeda, Y.; Kanaoka, Y. Liebigs Ann. Chem. 1989, 8, 781-788
42. Gowan, S. M.; Heald, R.; Stevens, M. F. G.; Kelland, L. R. Mol. Pharmcol. 2001, 60, 981-988
43. Stanslas, J.; Hagan, D. J.; Ellis, M. J.; Turner, C.; Carmichael, J.; Ward, W.; Hammonds, T. R.; Stevens, M. F. G. J. Med. Chem. 2000, 43, 1563-1572
44. Rummelt, S. M.; Ranocchiari, M.; van Bokhoven, J. A. Org. Lett. 2012, 14, 2188-2190
45. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460
46. Fagnoni, M.; Albini, A. Acc. Chem. Res. 2005, 38, 713-721
47. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305-308
48. Lipshutz, B. H.; Butler, T.; Swift, E. Org. Lett. 2008, 10, 697-700