CBr4: A Useful and Efficient Catalyst for One-Pot Synthesis of 4-Substituted-1,4,5,6,7,8-Hexahydroquinolin-5-ones Via Hantzsch Reaction
Jie Wu
Department of Chemistry, Fudan University, Shanghai 200433, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Tel.: 0086-021-55664619; Fax: 0086-021-65102412
Search for more papers by this authorWei-Zi Wang
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorWei Sun
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorJie Wu
Department of Chemistry, Fudan University, Shanghai 200433, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Tel.: 0086-021-55664619; Fax: 0086-021-65102412
Search for more papers by this authorWei-Zi Wang
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorWei Sun
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorAbstract
A carbon tetrabromide (CBr4) catalyzed one-pot synthesis of 4-substituted-1,4,5,6,7,8-hexahydroquinolin-5-one derivatives via a Hantzsch reaction under mild conditions was described.
REFERENCES
- 1 Dalko, P. I.; Moisan, L.. Angew. Chem., Int. Ed., 2004, 43, 5138.
- 2a Basavaiah, D.; Rao, A. J.; Satyanarayana, T.. Chem. Rev., 2003, 103, 811.
- 2b Tian, S.-K.; Hong, R.; Deng, L.. J. Am. Chem. Soc., 2003, 125, 9900.
- 2c Wu, J.; Sun, X.; Li, Y.. Eur. J. Org. Chem., 2005, 4271.
- 2d Wu, J.; Xia, H. G.. Green Chem., 2005, 7, 708.
- 3a Wu, J.; Sun, W.; Sun, X.; Xia, H. G.. Green Chem., 2006, 8, 365.
- 3b Yadav, J. S.; Reddy, B. V. S.; Harikishan, K.; Madan, C.; Narsaiah, A. V.. Synthesis, 2005, 2897.
- 3c Lee, A. S. Y.; Su, F. Y.. Tetrahedron Lett., 2005, 46, 6305.
- 3d Chen, M.-Y.; Lee, A. S. Y.. J. Chin. Chem. Soc., 2003, 50, 103.
- 3e Reddy, A. V.; Reddy, V. L. N.; Ravinder, K.; Venkateswarlu, Y.. Heteroycl. Commun., 2002, 8, 459.
- 3f Chen, M. Y.; Lu, K. C.; Lee, A. S. Y.; Lin, C. C.. Tetrahedron Lett., 2002, 43, 2777.
- 3g Chen, M. Y.; Lee, A. S. Y.. J. Org. Chem., 2002, 67, 1384.
- 3h Lee, A. S. Y.; Hu, Y. J.; Chu, S. F.. Tetrahedron, 2001, 57, 2121.
- 3i Abele, E.; Abele, R.; Lukevics, E.. J. Chem. Res., Synop., 1999, 624.
- 3j Lee, A. S. Y.; Cheng, C. L.. Tetrahedron, 1997, 53, 14255.
- 4a Schreiber, S. L.. Science, 2000, 287, 1964.
- 4b Mitchison, T. J.. Chem. Biol., 1994, 1, 3.
- 4c Schreiber, S. L.. Bioorg. Med. Chem., 1998, 6, 1127.
- 5a Mauzeral, D.; Westheimer, F. H.. J. Am. Chem. Soc., 1955, 77, 2261.
- 5b Baraldi, P. G.; Chiarini, A.; Budriesi, R.; Roberti, M.; Casolar, A.; Manfredini, S.; Simoni, D.; Zanirato, V.; Varani, K.; Borea, P. A.. Drug Des., 1989, 5, 13.
- 5c Baraldi, P. G.; Budriesi, R.; Cacciari, B.; Chiarini, A.; Garuti, L.; Giovanninetti, G.; Leoni, A.; Roberti, M.. Collect. Czech. Chem. Commun., 1992, 169.
- 5d Di Stilo, A.; Visentin, S.; Clara, C.; Gasco, A. M.; Ermondi, G.; Gasco, A.. J. Med. Chem., 1998, 41, 5393.
- 5e Kawase, M.; Shah, A.; Gaveriya, H.; Motohashi, N.; Sakagami, H.; Varga, A.; Molnar, J.. J. Bioorg. Chem., 2002, 10, 1051.
- 5f Suarez, M.; Verdecia, Y.; Illescas, B.; Martinez-Alvarez, R.; Avarez, A.; Ochoa, E.; Seoane, C.; Kayali, N.; Martin, N.. Tetrahedron, 2003, 59, 9179.
- 5g Shan, R.; Velazquez, C.; Knaus, E. E.. J. Med. Chem., 2004, 47, 254.
- 5h Sawada, Y.; Kayakiri, H.; Abe, Y.; Mizutani, T.; Inamura, N.; Asano, M.; Hatori, C.; Arsmori, I.; Oku, T.; Tanaka, H.. J. Med. Chem., 2004, 47, 2853.
- 6a Buhler, F. R.; Kiowski, W.. J. Hypertens., 1987, S3, 5.
- 6b Reid, J. L.; Meredith, P. A.; Pasanisi, F.. J. Cardiovasc. Pharmacol., 1985, S18, 7.
- 6c Godfraid, T.; Miller, R.; Wibo, M.. Pharmacol. Rev., 1986, 38, 321.
- 6d Sausins, A.; Duburs, G., Heterocycles, 1988, 27, 269.
- 6e Mager, P. P.; Coburn, R. A.; Solo, A. J.; Triggle, D. J.; Rothe, H., Drug Des. Discovery, 1992, 8, 273.
- 6f Mannhold, R.; Jablonka, B.; Voigdt, W.; Schoenafinger, K.; Schravan, K.. Eur. J. Med. Chem., 1992, 27, 229.
- 6g
Klusa, V..
Drugs Future,
1995,
20,
135.
10.1358/dof.1995.020.02.284117 Google Scholar
- 6h Bretzel, R. G.; Bollen, C. C.; Maeser, E.; Federlin, K. F.. Am. J. Kidney Dis., 1993, 21, 53.
- 6i
Bretzel, R. G.;
Bollen, C. C.;
Maeser, E.;
Federlin, K. F..
Drugs Future,
1992,
17,
465.
10.1358/dof.1992.017.06.175816 Google Scholar
- 6j Boer, R.; Gekeler, V.. Drugs Future, 1995, 20, 499.
- 7a Wu, J.; Zhang, L.; Diao, T. N.. Synlett, 2005, 2653.
- 7b Wu, J.; Wang, X.. Org. Biomol. Chem., 2006, 4, 1348.
- 7c Wu, J.; Zhang, L.; Luo, Y.. Tetrahedron Lett., 2006, 47, 6747.
- 8a
Hantzsch, A..
Ber. Dtsch. Chem. Ges.,
1888,
21,
942.
10.1002/cber.188802101180 Google Scholar
- 8b Hantzsch, A.. Ber. Dtsch. Chem. Ges., 1890, 23, 1747.
- 8c R. Wiley, H.; England, D. C.; Behr, L. C., In Organic Reactions Ed. by John Wiley, 1951, Vol. 6, p 367.
- 8d Dondoni, A.; Massi, A.; Minghini, E.; Bertolasi, V.. Tetrahedron, 2004, 60, 2311.
- 9a Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S.. Tetrahedron Lett., 2003, 44, 4129.
- 9b Wang, L. M.; Sheng, J.; Zhang, L.; Han, J. W.; Fan, Z.; Tian, H.; Qian, C. T.. Tetrahedron, 2005, 61, 1539.
- 9c Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C. F.. Tetrahedron Lett., 2005, 46, 5771.
- 9d Shastin, A. V.; Muzalevskii, V. M.; Korotchenko, V. N.; Balenkova, E. S.; Nenaidenko, V. G.. Russ. J. Org. Chem., 2006, 42, 183.
- 9e Ko, S.; Yao, C. F.. Tetrahedron, 2006, 62, 7293.
- 9f Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R.. Synthesis, 2006, 55.
- 10a Ji, S.-J.; Jiang, Z. Q.; Lu, J.; Loh, T. P.. Synlett, 2004, 831.
- 10b Sridhar, R.; Perumal, P. T.. Tetrahedron, 2005, 61, 2465.
- 11a Khadikar, B. M.; Gaikar, V. G.; Chitnavis, A. A.. Tetrahedron Lett., 1995, 36, 8083.
- 11b Ohberg, L.; Westman, J.. Synlett, 2001, 1296.
- 11c Agarwal, A.; Chauhan, P. M. S.. Tetrahedron Lett., 2005, 46, 1345.
- 12a Phillips, A. P.. J. Am. Chem. Soc., 1949, 71, 4003.
- 12b Anderson, G. J. R.; Berkelhammer, G.. J. Am. Chem. Soc., 1958, 80, 992.
- 12c Singh, H.; Chimni, D. S. S.; Kumar, S.. Tetrahedron, 1995, 51, 12775.
- 12d Gordeev, M. F.; Patel, D. V.; Gordon, E. M.. J. Org. Chem., 1996, 61, 924.
- 12e Breitenbucher, J. G.; Figliozzi, G.. Tetrahedron Lett., 2000, 41, 4311.
- 12f Liang, J. C.; Yeh, J. L.; Wang, C. S.; Liou, S. F.; Tasi, C. H.; Chen, I. J.. Bioorg. Med. Chem., 2002, 10, 719.
- 12g Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertoasi, V.. J. Org. Chem., 2003, 68, 6172.
- 12h Dondoni, A.; Massi, A.; Minghini, E.; Bertoasi, V.. Tetrahedron, 2004, 60, 2311.
- 12i Tewari, N.; Dwivedi, N.; Tripathi, R. P.. Tetrahedron Lett., 2004, 45, 9011.
- 12j Moseley, J. D.. Tetrahedron Lett., 2005, 46, 3179.