Synthesis of 1 H-indazoles and 1 H-pyrazoles via FeBr3/O 2 mediated intramolecular C-H amination

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 1317-1322

  Zhang, Tianshui ^a   Bao, Weiliang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOND FORMATION; C-H ACTIVATION; PYRAZOLES;

CHEMISTRY; ORGANIC COMPOUNDS;

CHEMICAL BONDS;

1 (2 FLUORO PHENYL) 3 PHENYL 1H INDAZOLE; 1 (4 NITRO PHENYL) 3 PHENYL 1H INDAZOLE; 1 PHENYL 3 4 TOLYL 1H INDAZOLE; 1,3 DIPHENYL 1H INDAZOLE; 1,3 DIPHENYL 5 (4 TOLYL) 1H PYRAZOLE; 1,3,5 TRIPHENYL 1H PYRAZOLE; 1H INDAZOLE DERIVATIVE; 1H PYRAZOLE DERIVATIVE; 3 (4 CHLORO PHENYL) 1 PHENYL 1H INDAZOLE; 3 (4 CHLORO PHENYL) 6 METHYL 1 PHENYL 1H INDAZOLE; 3 (4 NITRO PHENYL) 1 PHENYL 1H INDAZOLE; 3 METHYL 1 PHENYL 5 (4 TOLYL) 1H PYRAZOLE; 3 METHYL 1,5 DIPHENYL 1H PYRAZOLE; 3 PHENYL 1 4 TOLYL 1H INDAZOLE; 4 METHOXY 1,3 DIPHENYL 1H INDAZOLE; 5 (4 BROMO PHENYL) 3 METHYL 1 PHENYL 1H PYRAZOLE; 5 (4 CHLORO PHENYL) 3 METHYL 1 PHENYL 1H PYRAZOLE; 5 (4 CHLORO-PHENYL) 1,3 DIPHENYL 1H PYRAZOL; 5 (4 METHOXYPHENYL) 3 METHYL 1 PHENYL 1H PYRAZOLE; 5 METHYL 1 PHENYL 3 3 TOLYL 1H INDAZOLE; 6 CHLORO 3 (4 CHLORO PHENYL) 1 PHENYL 1H INDAZOLE; 6 FLUORO 3 (4 FLUORO PHENYL) 1 PHENYL 1H INDAZOLE; 6 METHOXY 1,3 DIPHENYL 1H INDAZOLE; 6 METHOXY 3 (4 METHOXY PHENYL) 1 PHENYL 1H INDAZOLE; 6 METHYL 1 PHENYL 3 4 TOLYL 1H INDAZOLE; 6 METHYL 1,3 DIPHENYL 1H INDAZOLE; 7 METHYL 1 PHENYL 3 3 TOLYL 1H INDAZOLE; INDAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; HYDRAZONE DERIVATIVE;

AMINATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; CATALYSIS; CHEMISTRY; CYCLIZATION; HYDROGEN BOND; SYNTHESIS;

AMINATION; CATALYSIS; CYCLIZATION; HYDRAZONES; HYDROGEN BONDING; INDAZOLES; PYRAZOLES;

MLCS; MLOWN;

EID: 84873344642     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3026862     Document Type: Article

References (43)

1. Bermudez, J.; Fake, C. S.; Joiner, G. F.; Joiner, K. A.; King, F. D.; Miner, W. D.; Sanger, G. J. J. Med. Chem. 1990, 33, 1924-1929
2. Moore, P. K.; Babbedge, R. C.; Wallace, P.; Gaffen, Z. A.; Hart, S. L. Br. J. Pharmacol. 1993, 108, 296-297
3. Boehm, H. -J.; Boehringer, M.; Bur, D.; Gmuender, H.; Huber, W.; Klaus, W.; Kostrwa, D.; Kuehne, H.; Luebbers, T.; Meunier-Keller, N.; Mueller, F. J. Med. Chem. 2000, 43, 2664-2674
4. Hartmann, M.; Sommer, M. E.; Keppler, B. K.; Kratz, F.; Einhäuser, Th. J. J. Inorg. Biochem. 1995, 59, 214
5. Clarke, M. J. Coord. Chem. Rev. 2003, 236, 209-233
6. Goodman, K. B.; Cui, H.; Dowdell, S. E.; Gaitanopoulos, D. E.; Ivy, R. L.; Sehon, C. A.; Stavenger, R. A.; Wang, G. Z.; Viet, A. Q.; Xu, W.; Ye, G.; Semus, S. F.; Evans, C.; Fries, H. E.; Jolivette, L. J.; Kirkpatrick, R. B.; Dul, E.; Khandekar, S. S.; Yi, T.; Jung, D. K.; Wright, L. L.; Smith, G. K.; Behm, D. J.; Bentley, R.; Doe, C. P.; Hu, E.; Lee, D. J. Med. Chem. 2007, 50, 6-9
7. Bekhit, A. A.; Abdel-Aziem, T. Bioorg. Med. Chem. 2004, 12, 1935-1945
8. Fustero, S.; Rosell, M. S.; Barrio, P.; Fuentes, A. S. Chem. Rev. 2011, 111, 6984
9. Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Bioorg. Med. Chem. Lett. 2005, 15, 1793-1797
10. Sperandeo, N. R.; Brun, R. ChemBioChem 2003, 4, 69
11. Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824
12. Sun, J. -H.; Teleha, C. A.; Yan, J. -S.; Rodgers, J. D.; Nugiel, D. A. J. Org. Chem. 1997, 62, 5627-5629
13. Rodgers, J. D.; Johnson, B. L.; Wang, H.; Greenberg, R. A.; Erickson-Viitanen, S.; Klabe, R. M.; Cordova, B. C.; Rayner, M. M.; Lam, G. N.; Chang, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 2919-2921
14. Corsi, G.; Palazzo, G.; Germani, C.; Barcellona, P. S.; Silvestrini, B. J. Med. Chem. 1976, 19, 778-783
15. Guglielmotti, A.; De Joannon, A. C.; Cazzolla, N.; Marchetti, M.; Soldo, L.; Cavallo, G.; Pinza, M. Pharmacol. Res. 1995, 32, 369-373
16. Wrobleski, S. T.; Chen, P.; Hynes, J., Jr.; Lin, S.; Norris, D. J.; Pandit, C. R.; Spergel, S.; Wu, H.; Tokarski, J. S.; Chen, X.; Gilloly, K. M.; Kiener, P. A.; McIntyre, K. W.; Patil-Koota, V.; Shuster, D. J.; Turk, L. A.; Yang, G.; Leftheris, K. J. Med. Chem. 2003, 46, 2110-2116
17. Yates, C. M.; Brown, P. J.; Stewart, E. L.; Patten, C.; Austin, R. J. H.; Holt, J. A.; Maglich, J. M.; Angell, D. C.; Sasse, R. Z.; Taylor, S. J.; Uings, I. J.; Trump, R. P. J. Med. Chem. 2010, 53, 4531
18. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347-1365
19. Huisgen, R.; Bast, K. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, 650
20. Stadlbauer, W. Sci. Synth. 2002, 12, 227-324
21. Crestey, F.; Collot, V.; Stiebing, S.; Rault, S. Tetrahedron 2006, 62, 7772
22. Jin, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 3323-3325
23. Liu, Z.; Shi, F.; Martinez, P. D. G.; Raminelli, C.; Larock, R. C. J. Org. Chem. 2008, 73, 219-226
24. Spiteri, C.; Keeling, S.; Moses, J. E. Org. Lett. 2010, 12, 3368-3371
25. Wray, B. C.; Stambuli, J. P. Org. Lett. 2010, 12, 4576-4579
26. Xiong, X.; Jiang, Y.; Ma, D. Org. Lett. 2012, 14, 2552-2555
27. Li, P.; Wu, C.; Zhao, J.; Rogness, D. C.; Shi, F. J. Org. Chem. 2012, 77, 3149-3158
28. Jin, W.; Yu, H.; Yu, Z. Tetrahedron Lett. 2011, 52, 5884-5887
29. Liu, P.; Pan, Y.; Xu, Y.; Wang, H. Org. Biomol. Chem. 2012, 10, 4696-4698
30. Guo, S.; Wang, J.; Guo, D.; Zhang, X.; Fan, X. RSC Adv. 2012, 2, 3772-3777
31. Gosselin, F.; O'Shea, P. D.; Webster, R. A.; Reamer, R. A.; Tillyer, R. D.; Grabowski, E. J. Synlett 2006, 19, 3267-3270
32. Gladstone, W. A. F.; Norman, R. O. C. J. Chem. Soc. 1965, 3048-3052
33. Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931-2934
34. Hu, J.; Chen, S.; Sun, Y.; Yang, J.; Rao, Y. Org. Lett. 2012, 14, 5030-5033
35. Correa, A.; Mancheño, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108-1117
36. Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217-6254
37. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317-3321
38. Salovich, J. M.; Lindsley, C. W.; Hopkins, C. R. Tetrahedron Lett. 2010, 51, 3796-3799
39. Hattori, K.; Yamaguchi, K.; Yamaguchi, J.; Itami, K. Tetrahedron 2012, 68, 7605-7612
40. Dvorak, C. A.; Rudolph, D. A.; Ma, S.; Carruthers, N. I. J. Org. Chem. 2005, 70, 4188-4190
41. Kovelesky, A. C.; H. Shine, J. J. Org. Chem. 1988, 53, 1973
42. Moegel, L.; Schulz, M.; Radeglia, R.; Osten, H. J. J. Prakt. Chem. (Leipzig) 1984, 326, 54-62
43. Sabitha, G.; Kiran Kumar Reddy, G. S.; Reddy, Ch. S.; Fatima, N.; Yadav, J. S. Synthesis 2003, 8, 1267-1271