Pd-catalyzed tandem C-H azidation and N-N bond formation of arylpyridines: A direct approach to pyrido[1,2-b ]indazoles

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4262-4265

  Zheng, Qing Zhong ^a   Feng, Peng ^a   Liang, Yu Feng ^a   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; INDAZOLE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; PYRIDO(1,2 B)INDAZOLE; PYRIDO(1,2-B)INDAZOLE;

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

AZIDES; CATALYSIS; HYDROGEN BONDING; INDAZOLES; MOLECULAR STRUCTURE; PALLADIUM; PYRIDINES;

EID: 84882801418     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402060q     Document Type: Article

References (77)

1. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
2. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
3. Lu, H.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899
4. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
5. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
6. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
7. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
8. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
9. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
10. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
11. Shiotani, A.; Itatani, H. Angew. Chem., Int. Ed. 1974, 13, 471
12. Liégault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022
13. Sridharan, V.; Martín, M. A.; Menéndez, J. C. Eur. J. Org. Chem. 2009, 4614
14. Yeung, C. S.; Zhao, X.; Borduas, N.; Dong, V. M. Chem. Sci. 2010, 1, 331
15. Morimoto, K.; Itoh, M.; Hirano, K.; Satoh, T.; Shibata, Y.; Tanaka, K.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 5359
16. Li, H.; Zhu, R.-Y.; Shi, W.-J.; He, K.-H.; Shi, Z.-J. Org. Lett. 2012, 14, 4850
17. Zhao, J.; Wang, Y.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2012, 14, 1078
18. Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250
19. Samanta, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2011, 50, 5217
20. Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504
21. Kuninobu, Y.; Yoshida, T.; Takai, K. J. Org. Chem. 2011, 76, 7370
22. Youn, S. W.; Bihn, J. H.; Kim, B. S. Org. Lett. 2011, 13, 3738
23. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996
24. Ureshino, T.; Yoshida, T.; Kuninobu, Y.; Takai, K. J. Am. Chem. Soc. 2010, 132, 14324
25. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184
26. Tsang, W. C. P.; Munday, R. H.; Brasche, G.; Zheng, N.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7603
27. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560
28. Xiong, T.; Li, Y.; Bi, X.; Lv, Y.; Zhang, Q. Angew. Chem., Int. Ed. 2011, 50, 7140
29. Zhang, H.; Shi, R.; Gan, P.; Liu, C.; Ding, A.; Wang, Q.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5204
30. The information on the following drug and drug candidates, please visit the PubChem website (http://pubchem.ncbi.nlm.nih.gov/), which provides the compound structure, bioactivity, published studies, and information regarding ongoing clinical trials, applications, and usage: niraparib, granisetron, pazopanib, linifanib, axitinib, and GDC-0941.
31. De Angelis, M.; Stossi, F.; Carlson, K. A.; Katzenellenbogen, B. S.; Katzenellenbogen, K. A. J. Med. Chem. 2005, 48, 1132
32. Timári, G.; Soós, T.; Hajós, G.; Messmer, A.; Nacsa, J.; Molnár, J. Bioorg. Med. Chem. Lett. 1996, 6, 2831
33. Phillips, S. D.; Castle, R. N. J. Heterocycl. Chem. 1980, 17, 1489
34. Reddy, Y. P.; Reddy, G. S.; Reddy, K. K. Indian J. Chem., Sect. B 1977, 15B, 1133
35. Abramovitch, R. A.; Kalinowski, J. J. Heterocycl. Chem. 1974, 11, 857
36. Cadogan, J. I. G.; Cameron-Wood, M.; Mackie, R. K.; Searle, R. J. G. J. Chem. Soc. 1965, 4831
37. Cadogan, J. I. G.; Cameron-Wood, M. Proc. Chem. Soc., London 1962, 361
38. Abramovitch, R. A.; Adams, K. A. H. Can. J. Chem. 1961, 39, 2516
39. Abramovitch, R. A.; Ahmad, Y.; Newman, D. Tetrahedron Lett. 1961, 2, 752
40. Zhao, J.; Wu, C.; Li, P.; Ai, W.; Chen, H.; Wang, C.; Larock, R. C.; Shi, F. J. Org. Chem. 2011, 76, 6837
41. Driver, T. G. Org. Biomol. Chem. 2010, 8, 3831
42. Cenini, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234
43. Katsuki, T. Chem. Lett. 2005, 34, 1304
44. Nguyen, Q.; Nguyen, T.; Driver, T. G. J. Am. Chem. Soc. 2013, 135, 620
45. Nguyen, Q.; Sun, K.; Driver, T. G. J. Am. Chem. Soc. 2012, 134, 7262
46. Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 133, 4702
47. Ichinose, M.; Suematsu, H.; Yasutomi, Y.; Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2011, 50, 9884
48. Bonnamour, J.; Bolm, C. Org. Lett. 2011, 13, 2012
49. Lu, H.; Jiang, H.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2010, 49, 10192
50. Shou, W. G.; Li, J.; Guo, T.; Lin, Z.; Jia, G. Organometallics 2009, 28, 6847
51. Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2013, 52, 1739
52. Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2013, 15, 1638
53. Kim, J. Y.; Park, S. H.; Ryu, J.; Cho, S. H.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110
54. Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 9904
55. Shi, J.; Zhou, B.; Yang, Y.; Li, Y. Org. Biomol. Chem. 2012, 10, 8953
56. Qin, C.; Shen, T.; Tang, C.; Jiao, N. Angew. Chem., Int. Ed. 2012, 51, 6971
57. Jiang, Z.; Lu, P.; Wang, Y. Org. Lett. 2012, 14, 6266
58. Shen, Y.; Han, C.; Cai, S.; Lu, P.; Wang, Y. Tetrahedron Lett. 2012, 53, 5671
59. Lyaskovskyy, V.; Suarez, A. I. O.; Lu, H.; Jiang, H.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2011, 133, 12264
60. Qin, C.; Zhou, W.; Chen, F.; Ou, Y.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 12595
61. Chen, F.; Qin, C.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11487
62. Wang, Y.-F.; Toh, K. K.; Ng, E. P. J.; Chiba, S. J. Am. Chem. Soc. 2011, 133, 6411
63. Wang, Y.-F.; Toh, K. K.; Lee, J.-Y.; Chiba, S. Angew. Chem., Int. Ed. 2011, 50, 5927
64. Gu, J.; Xiong, W.; Zhang, Z.; Zhu, S. Synthesis 2011, 1717
65. Xiong, W.; Zhang, H.; Xin, Y.; Zhu, S. Tetrahedron 2011, 67, 2232
66. Lu, H.; Subbarayan, V.; Tao, J.; Zhang, X. P. Organometallics 2010, 29, 389
67. Qin, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 15893
68. Song, W.; Lei, M.; Shen, Y.; Cai, S.; Lu, W.; Lu, P.; Wang, Y. Adv. Synth. Catal. 2010, 352, 2432
69. Zhou, W.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094
70. Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961
71. Yu, D.-G.; Suri, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 8802
72. Tang, C.; Jiao, N. J. Am. Chem. Soc. 2012, 134, 18924
73. Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436
74. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
75. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066
76. Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806
77. Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300