An efficient synthesis of 2H-indazoles via reductive cyclization of 2-nitrobenzylamines induced by low-valent titanium reagent

Tetrahedron

Volumn 68, Issue 20, 2012, Pages 3851-3855

  Sun, Fang ^a   Feng, Xian ^a   Zhao, Xuan ^a   Huang, Zhi Bin ^a   Shi, Da Qing ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

2 Nitrobenzylamine; 2H Indazole; Low valent titanium reagent; Reductive cyclization

Indexed keywords

BENZYLAMINE DERIVATIVE; INDAZOLE DERIVATIVE; TITANIUM DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; PH; PRIORITY JOURNAL; REDUCTION;

EID: 84859790153     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.043     Document Type: Article

References (44)

1. (a) Keppler, B. K.; Hartmann, M. Met.-Based Drugs 1994, 1, 145-150;
2. (b) Baraldi, P. G.; Balboni, G.; Pavani, M. G.; Spalluto, G.; Tabrizi, M. A.; Clercq, E. D.; Balzarini, J.; Bando, T.; Sugiyama, H.; Romagnoli, R. J. Med. Chem. 2001, 44, 2536-2543;
3. (c) Qian, S. J.; Cao, J.; Yan, Y.; Sun, M.; Zhu, H.; Hu, Y.; He, Q.; Yang, B. Mol. Cell Biochem. 2010, 345, 13-21.
4. (a) Sun, J. H.; Teleha, C. A.; Yan, J. S.; Rodgers, J. D.; Nugiel, D. A. J. Org. Chem. 1997, 62, 5627-5629;
5. (b) Rodgers, J. D.; Johnson, B. L.; Wang, H.; Greenberg, R. A.; Erickson-Viitanen, S.; Klabe, R. M.; Cordova, B. C.; Rayer, M. M.; Lam, G. N.; Chang, C. H. Bioorg. Med. Chem. Lett. 1996, 6, 2919-2924.
6. Ikeda, Y.; Takano, N.; Matsushita, H.; Shiraki, Y.; Koide, T.; Nagashima, R.; Fujimura, Y.; Shindo, M.; Suzuki, S.; Iwasaki, T. Arzneim.-Forsch. 1979, 29, 511-520.
7. Li, X.; Chu, S.; Feher, V. A.; Khalili, M.; Nie, Z.; Margosiak, S.; Nikulin, V.; Levin, J.; Sparankle, K. G.; Fedder, M. E.; Almassy, R.; Appelt, K.; Yager, K. M. J. Med. Chem. 2003, 46, 5663-5673.
8. (a) Bistochi, G. A.; De Meo, G.; Pedini, M.; Ricci, A.; Brouilhet, H.; Bucherie, S.; Rabaud, M.; Jacquignon, P. Farmaco Ed. Sci. 1981, 36, 315-333;
9. (b) Picciola, G.; Ravenna, F.; Carenini, G.; Gentili, P.; Riva, M. Farmaco Ed. Sci. 1981, 36, 1037-1056.
10. Corsi, G.; Palazzo, G.; Germani, C.; Barcellona, P. S.; Silvestrini, B. J. Med. Chem. 1976, 19, 778-783.
11. (a) Albini, A.; Bettinetti, G.; Minoli, G. Heterocycles 1988, 27, 1207-1216;
12. (b) Seela, F.; Bourgeois, W. Helv. Chim. Acta 1991, 74, 315-322;
13. (c) Cerrada, M. L.; Elguero, J.; de le Fuente, J.; Pardo, C.; Ramos, M. Synth. Commun. 1993, 23, 1947-1952;
14. (d) Rosevear, J.; Wilshire, J. F. K. Aust. J. Chem. 1991, 44, 1097-1114;
15. (e) Akazome, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1994, 59, 3375-3380;
16. (f) Song, J. J.; Yee, N. K. Org. Lett. 2000, 2, 519-521;
17. (g) Sawant, D.; Kumar, R.; Maulik, P. R.; Kundu, B. Org. Lett. 2006, 8, 1525-1528;
18. (h) Wu, C.; Fang, Y.; Larock, R. C.; Shi, F. Org. Lett. 2010, 12, 2234-2237;
19. (i) Haag, B.; Peng, Z.; Knochel, P. Org. Lett. 2009, 11, 4270-4273;
20. (j) Halland, N.; Nazare, M.; Rkyek, O.; Alonso, J.; Urmann, M.; Lindenschmidt, A. Angew. Chem., Int. Ed. 2009, 48, 6879-6882;
21. (k) Stokes, B. J.; Vogel, C. V.; Urnezis, L. K.; Pan, M.; Driver, T. G. Org. Lett. 2010, 12, 2884-2887;
22. (l) Kumar, M. R.; Park, A.; Park, N.; Lee, S. Org. Lett. 2011, 13, 3542-3545.
23. (a) Paal, C.; Krecke, F. Chem. Ber. 1890, 23, 2640-2641;
24. (b) Paal, C. Chem. Ber. 1891, 24, 959-966;
25. (c) Busch, V.; Hartman, P. J. Prakt. Chem. 1895, 2, 404-406;
26. (d) Campi, E. M.; Habsuda, J.; Jackson,W. R.; Cartrin, A. M.; McCubbin, Q. J. Aust. J. Chem. 1995, 48, 2023-2033.
27. Frontana-Oribe, B. A.; Moinet, C. Tetrahedron 1998, 54, 3197-3206.
28. Mills, A. D.; Nazer, M. Z.; Haddadin, M. J.; Kurth, M. J. J. Org. Chem. 2006, 71, 2687-2689.
29. Shi, D. Q.; Dou, G. L.; Ni, S. N.; Shi, J. W.; Li, X. Y.; Wang, X. S.; Wu, H.; Ji, S. J. Synlett 2007, 2509-2512.
30. (a) McMurry, J. E. Acc. Chem. Res. 1974, 7, 281-286;
31. (b) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405-411;
32. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513-1524.
33. (a) Lenoir, D. Synthesis 1989, 883-897;
34. (b) Fürstner, A.; Bogdanovi, B. Angew. Chem., Int. Ed. 1996, 35, 2442-2469;
35. (c) Shi, D. Q.; Chen, J. X.; Chai, W. Y.; Chen, W. X.; Kao, T. Y. Tetrahedron Lett. 1993, 34, 2863-2864.
36. Shi, D. Q.; Rong, R. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hu, H. W. Tetrahedron Lett. 2003, 44, 3199-3201.
37. (a) Shi, D. Q.; Dou, G. L.; Shi, C. L.; Li, Z. Y.; Ji, S. J. Synthesis 2007, 3117-3124;
38. (b) Dou, G. L.; Shi, D. Q. J. Comb. Chem. 2008, 10, 810-813.
39. Shi, D. Q.; Dou, G. L.; Li, Z. Y.; Ni, S. N.; Li, X. Y.; Wang, X. S.; Wu, H.; Ji, S. J. Tetrahedron 2007, 63, 9764-9773.
40. Shi, D. Q.; Rong, S. F.; Dou, G. L.; Wang, M. M. J. Comb. Chem. 2010, 12, 25-30.
41. Shi, D. Q.; Rong, S. F.; Dou, G. L. Synth. Commun. 2010, 40, 2302-2310.
42. Zhao, X.; Shi, D. Q. J. Heterocycl. Chem. 2011, 48, 634-638.
43. Dou, G. L.; Shi, D. Q. J. Comb. Chem. 2009, 11, 1073-1077.
44. 2=0.2372.