Synthesis of aza-fused polycyclic quinolines via double C-H bond activation

Chemistry - A European Journal

Volumn 18, Issue 29, 2012, Pages 8896-8900

  Huang, Ji Rong ^a   Dong, Lin ^a   Han, Bo ^b   Peng, Cheng ^b   Chen, Ying Chun ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

alkynes; annulation; aza fused polycyclic quinolines; C H activation; heterocycles; rhodium

Indexed keywords

ALKYNES; ANNULATION; AZA-FUSED POLYCYCLIC QUINOLINES; C-H ACTIVATION; HETEROCYCLES;

ACETYLENE; RHODIUM; RHODIUM COMPOUNDS;

ACTIVATION ANALYSIS;

COPPER; HETEROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON; QUINOLINE DERIVATIVE; RHODIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGEN BOND; SYNTHESIS;

AZA COMPOUNDS; COPPER; CYCLIZATION; HYDROGEN BONDING; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; QUINOLINES; RHODIUM;

EID: 84863666065     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201207     Document Type: Article

References (74)

1. A. T. Balaban, D. C. Oniciu, A. R. Katritzky, Chem. Rev. 2004, 104, 2777
2. J. A. Joule, K. Mills, Heterocyclic Chemistry, 5 th ed., John Wiley & Sons, Chichester, 2010.
3. V. U. Shenoy, S. Seshardi, Dyes Pigm. 1989, 11, 137
4. J. Novotny, C. H. Collins, F. W. Starks, J. Pharm. Sci. 1974, 63, 1264.
5. D. Guenther, (Hoechst AG, Germany), US Patent 4,124,589, 1978.
6. D. Guenther, R. Erckel, H. Fruehbeis, (Hoechst AG, Germany), US Patent 4,219,651, 1980.
7. M. Boiani, M. Gonzalez, Mini-Rev. Med. Chem. 2005, 5, 409.
8. T. L. Amyes, S. T. Diver, J. P. Richard, F. M. Rivas, K. Toth, J. Am. Chem. Soc. 2004, 126, 4366.
9. M. Hranjec, M. Kralj, I. Piantanida, M. Sedić, L. Šuman, K. Pavelić, G. Karminski-Zamola, J. Med. Chem. 2007, 50, 5696.
10. G. Morgan, J. Stewart, J. Chem. Soc. 1938, 1292
11. E. M. Roberts, M. Gates, V. Boekelheide, J. Org. Chem. 1955, 20, 1443
12. G. Cooper, W. J. Irwin, J. Chem. Soc. Perkin Trans. 1 1975, 798
13. C. Venkatesh, G. S. M. Sundaram, H. Ila, H. Junjappa, J. Org. Chem. 2006, 71, 1280
14. M. Hranjec, G. Karminskin-Zamola, Molecules 2007, 12, 1817
15. T. Benincori, F. Sannicolò, J. Heterocycl. Chem. 1988, 25, 1029
16. A. Li, T. M. Gilbert, D. A. Klumpp, J. Org. Chem. 2008, 73, 3654
17. S. P. J. M. van Nispen, C. Mensink, A. M. van Leusen, Tetrahedron Lett. 1980, 21, 3723
18. M. Abass, Heterocycles 2005, 65, 901
19. V. V. Kouznetsov, L. Y. V. Mendez, C. M. M. Gomez, Curr. Org. Chem. 2005, 9, 141
20. Q. Cai, Z.-Q. Li, J.-J. Wei, L.-B. Fu, C.-Y. Ha, D.-Q. Pei, K. Ding, Org. Lett. 2010, 12, 1500
21. B.-W. Zhou, J.-R. Gao, D. Jiang, J.-H. Jia, Z.-P. Yang, H.-W. Jin, Synthesis 2010, 2794
22. Q. Liao, L.-Y. Zhang, S.-T. Li, C.-J. Xi, Org. Lett. 2011, 13, 228.
23. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
24. K. S. Masters, T. R. M. Rauws, A. K. Yadav, W. A. Herrebout, B. V. D. Veken, B. U. W. Maes, Chem. Eur. J. 2011, 17, 6315
25. H.-G. Wang, Y. Wang, C.-L. Peng, J.-C. Zhang, Q. Zhu, J. Am. Chem. Soc. 2010, 132, 13217
26. Y. Nakao, K.-S. Kanyiva, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2006, 128, 8146
27. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
28. O. Daugulis, Top. Curr. Chem. 2009, 292, 57
29. L, Ackermann, Chem. Commun. 2010, 46, 4866
30. K. Fagnou, Top. Curr. Chem. 2009, 292, 35.
31. G.-Y. Song, X. Gong, X.-W. Li, J. Org. Chem. 2011, 76, 7583
32. M. Shimizu, H. Tsurugi, T. Satoh, M. Miura, Chem. Asian J. 2008, 3, 881
33. M. Imai, M. Tanaka, S. Nagumo, N. Kawahara, H. Suemune, J. Org. Chem. 2007, 72, 2543
34. R. T. Stemmler, C. Bolm, Adv. Synth. Catal. 2007, 349, 1185
35. S. Mochida, M. Shimizu, K. Hirano, T. Satoh, M. Miura, Chem. Asian J. 2010, 5, 847
36. T. Uto, M. Shimizu, K. Ueura, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 298
37. T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Commun. 2009, 5141
38. D. A. Colby, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 3645
39. L. Li, W. W. Brennessel, W. D. Jones, J. Am. Chem. Soc. 2008, 130, 12414
40. N. Guimond, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 12050
41. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474
42. N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. 2008, 120, 4083
43. Angew. Chem. Int. Ed. 2008, 47, 4019
44. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2011, 123, 4255
45. Angew. Chem. Int. Ed. 2011, 50, 4169
46. P. C. Too, Y.-F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688
47. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326
48. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, in press; DOI
49. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. Int. Ed. 2012, 51, 3948
50. N. Umeda, K. Hirano, T. Satoh, N. Shibata, H. Sato, M. Miura, J. Org. Chem. 2011, 76, 13
51. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212
52. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407
53. G.-Y. Song, F. Wang, X.-W. Li, Chem. Soc. Rev. 2012, 41, 3651.
54. L. Ackermann, R. Vicente, Top. Curr. Chem. 2009, 292, 211
55. L. Ackermann, A. V. Lygin, N. Hofmann, Angew. Chem. 2011, 123, 6503
56. Angew. Chem. Int. Ed. 2011, 50, 6379
57. B. Li, H.-L. Feng, S.-S. Xu, B.-Q. Wang, Chem. Eur. J. 2011, 17, 12573
58. L. Ackermann, S. Fenner, Org. Lett. 2011, 13, 6548.
59. M. Yamashita, H. Horiguchi, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7481
60. M. Yamashita, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 2337
61. L. Ackermann, A. V. Lygin, N. Hofmann, Org. Lett. 2011, 13, 3278.
62. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
63. K.-L. Tan, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 3202
64. S. H. Wiedemann, J. C. Lewis, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2006, 128, 2452.
65. During the final preparation of this manuscript, Chang and co-workers reported a rhodium(I) catalyst system for the addition of heteroarenes to both alkenes and alkynes, see:, J. Ryu, S.-H. Cho, S. Chang, Angew. Chem. 2012, 124, 3737
66. Angew. Chem. Int. Ed. 2012, 51, 3677.
67. H. Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404
68. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900
69. D.-B. Zhao, W.-H. Wang, F. Yang, J.-B. Lan, L. Yang, G. Gao, J.-S. You, Angew. Chem. 2009, 121, 3346
70. Angew. Chem. Int. Ed. 2009, 48, 3296
71. F. Besselièvre, S. Piguel, Angew. Chem. 2009, 121, 9717
72. Angew. Chem. Int. Ed. 2009, 48, 9553
73. M. Miyasaka, K. Hirano, T. Satoh, R. Kowalczyk, C. Bolm, M. Miura, Org. Lett. 2011, 13, 359
74. P.-H. Xi, F. Yang, S. Qin, D.-B. Zhao, J. B. Lan, G. Gao, C.-W. Hu, J.-S. You, J. Am. Chem. Soc. 2010, 132, 1822.