Assembly of N, N -disubstituted hydrazines and 1-aryl-1 H-indazoles via copper-catalyzed coupling reactions

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2552-2555

  Xiong, Xiaodong ^a   Jiang, Yongwen ^b   Ma, Dawei ^b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; CUPROUS IODIDE; DRUG DERIVATIVE; HYDRAZINE DERIVATIVE; INDAZOLE DERIVATIVE; IODIDE; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; HYDRAZINES; INDAZOLES; IODIDES; MOLECULAR STRUCTURE; PROLINE;

EID: 84862060671     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300847v     Document Type: Article

References (51)

1. Hamlyn, R.; Huckstep, M.; Lynch, R.; Stokes, S.; Tickle, D.; Patient, L. Azacyclic Compounds As Inhibitors of Sensory Neurone Specific Channels. WO 2005005392, January 20, 2005.
2. Kuratani, K.; Nakahama, K.; Morita, I.; Murota, S. Phenylhydrazine derivative and cytotoxic preventive. JP 09110815, April 28, 1997.
3. Hong, S.; Bavadekar, S.; Lee, S.; Patil, P.; Lalchandani, S.; Feller, D.; Miller, D. Bioorg. Med. Chem. Lett. 2005, 15, 4691
4. Werner, M.; Dieter, D.; Chistos, T.; Christopher, B.; Bertram, C.; Johannes, G. Semicarbazide Derivatives for Combating Thromboembolic Diseases. US 20050171102, April 7, 2003.
5. Hamanaka, N.; Takahashi, K.; Nagao, Y.; Torisu, K.; Shigeoka, S.; Hamada, S.; Kato, H.; Tokumoto, H.; Kondo, K. Bioorg. Med. Chem. Lett. 1995, 5, 1087
6. Blumenfeld, M.; Compere, D.; Gauthier, J. Improvements Relating to Fabric Treatment Compositions. WO 2009065893, September 21, 2011.
7. Sasikumar, T.; Burnett, D.; Zhang, H.; Smith-Torhan, A.; Fawzi, A.; Lachowicz, J. Bioorg. Med. Chem. Lett. 2006, 16, 4543
8. Nicolo, V.; Vincenzo, F.; Silvestre, B.; Michele, R. J. Heterocyclic Chem. 1985, 22, 97
9. Song, J.; Yee, N. Org. Lett. 2000, 2, 519
10. Wagaw, S.; Yang, B.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251
11. Okiko, M.; Norihiko, T.; Yasuo, K.; Yoshiji, T.; Norimitsu, T.; Mikiji, M.; Takeaki, N. Tetrahedron 2006, 62, 3629
12. Thorsten, G.; Julio L, F.; Solveig A, S.; Hubert, W.; Lutz H, G. Angew. Chem., Int. Ed. 2011, 50, 5757
13. Blatter, H.; Lukaszewskl. Tetrahedron Lett. 1968, 22, 2701
14. Waldrep, T.; Rieder, B.; Thibault, T.; Canada, E. J. Agric. Food Chem. 1991, 39, 392
15. Elliott, A. J. Org. Chem. 1980, 45, 3677
16. Poirier, R.; Benington, F. J. Am. Chem. Soc. 1952, 74, 3192
17. Peter A. S, S.; Norman W, K. J. Org. Chem. 1958, 23, 1599
18. Suzuki, H.; Yamamoto, A. J. Chem. Res., Synop. 1992, 280
19. Wagaw, S.; Yang, B.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621
20. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2090
21. Loog, O.; Maeorg, U.; Ragnarsson, U. Synthesis 2000, 1591
22. Yutaka, A.; Yuko, S.; Takeshi, S.; Yasuo, K. Synth. Commun. 2000, 30, 131
23. Starkov, P.; Zemskov, I.; Sillard, R.; Tšubrik, O.; Mäeorg, U. Tetrahedron Lett. 2007, 48, 1155
24. Kisseljova, K; Tšubrik, O.; Sillard, R.; Mäeorg, S.; Mäeorg, U. Org. Lett. 2006, 8, 43
25. Tsubrik, O.; Sillard, R.; Maeorg, U. Synthesis 2006, 15, 843
26. Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222
27. Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Ma, D. Org. Lett. 2009, 11, 5250
28. Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 4542
29. Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem., Int. Ed. 2011, 50, 1118
30. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803
31. Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48, 348
32. Cortes, M.; Nguyen, B.; Cuevas, J.; Pennypacker, K.; Antilla, J. C. Org. Lett. 2010, 12, 1316
33. Racine, E.; Monnier, F.; Vors, J.; Taillefer, M. Org. Lett. 2011, 13, 2818
34. Cai, Q.; Zou, B.; Ma, D. Angew. Chem., Int. Ed. 2006, 45, 1276
35. Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050
36. Zhao, H.; Fu, H.; Qiao, R. J. Org. Chem. 2010, 75, 3311
37. Xu, W.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. Org. Lett. 2011, 13, 1274
38. Zhang, X. Q.; Song, F. B.; Kuo, G. H.; Xiang, A.; Gibbs, A. C.; Abad, M. C.; Sun, W. M.; Kuo, L. C.; Sui, Z. H. Bioorg. Med. Chem.. 2011, 21, 4762
39. Chen, H.; Kuo, S.; Teng, C.; Lee, F.; Wang, J.; Lee, Y.; Kuo, C.; Huang, C.; Wu, C.; Huang, L. Bioorg. Med. Chem.. 2008, 16, 1262
40. Bharate, S. B.; Mahajan, T. R.; Gole, Y. R.; Nambiar, M.; Matan, T. T.; Almeida, A. K.; Balachandran, S.; Junjappa, H.; Balakrishnan, A.; Vishwakarma, R. A. Bioorg. Med. Chem. 2008, 16, 7167
41. Dessole, G.; Branca, D.; Ferrigno, F.; Kinzel, Q.; Muraglia, E.; Palumbi, M. C.; Rowley, M.; Serafini, S.; Steinkuhler, C.; Jones, P. Bioorg. Med. Chem. Lett. 2009, 19, 4191
42. Song, J. J.; Yee, N. K. Org. Lett. 2000, 2, 519
43. Song, J. J.; Yee, N. K. Tetrahedron Lett. 2001, 42, 2937
44. Lebedev, A. Y.; Khartulyari, A. S.; Voskoboynikov, A. Z. J. Org. Chem. 2005, 70, 596
45. Cho, C. S.; Lim, D. K.; Heo, N. H.; Kim, T. J.; Shim, S. C. Chem. Commun. 2004, 104
46. Viña, D.; Olmo, E. D.; López-pérez, J. L.; Feliciano, A. S. Org. Lett. 2007, 9, 525
47. Spiteri, C.; Keeling, S.; Moses, J. E. Org. Lett. 2010, 12, 3368
48. Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 3323
49. Stambuli, J. P.; Wray, B. C. Org. Lett. 2010, 12, 4576
50. Liu, R.; Zhu, Y.; Qin, L.; Ji., S. Synth. Commun. 2008, 38, 249
51. Gao, M.; Liu, X.; Wang, X.; Cai, Q.; Ding, K. Chin. J. Chem. 2011, 29, 1199