Efficient solvent-free synthesis of quinolines promoted by BiCl3

Letters in Organic Chemistry

Volumn 3, Issue 4, 2006, Pages 289-291

  Jia, Cheng Sheng ^a   Wang, Guan Wu ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

methylene ketones; BiCl3; Friedl nder reaction; O aminoaryl ketones; Quinoline; Solvent free

Indexed keywords

EID: 33746146972     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806776114568     Document Type: Article

References (36)

1. (a) Michael, J. P. Nat. Prod Rep., 1997, 14, 605
2. (b) Subbaraju, G. V.; Kavitha, J.; Rajasekhar, D.; Jimenez, J. I. J. Nat. Prod, 2004, 67, 461
3. (c) Zaragoza, F.; Stephensen, H.; Peschke, B.; Rimvall, K. J. Med. Chem., 2005, 48, 306.
4. (a) Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 5, pp. 167-243
5. (b) Amii, H.; Kishikawa, Y.; Uneyama, K. Org, Lett., 2001, 3, 1109.
6. Manske, R. H. Chem. Rev., 1942, 30, 113.
7. Friedländer, P. Berichte der Deutschem Chemischen Gesellschaft., 1882, 15, 2572.
8. For reviews, see: a Fehnel, E. A. J. Heterocycl. Chem., 1967, 4, 565
9. (b) Cheng, C.-C.; Yen, S.-J. Org. React., 1982, 28, 37.
10. (a) Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem., 1994, 37, 2129
11. (b) Kalluraya, B.; Sreenivasa, S. Farmaco, 1998, 53, 399;
12. (c) Gladiali, S.; Chelucci, G.; Mudadu, M. S.; Gastaut M.-A.; Thummel, R. P. J. Org. Chem., 2001, 66, 400
13. (d) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem, 2003, 68, 467.
14. (a) Sliskovic, D. R.; Picard, J. A.; Roark, W. H.; Roth, B. D.; Ferguson, E.; Krause, B. R.; Newton, R. S.; Sekerke, C.; Shaw, M. K. J. Med Chem, 1991, 34, 367
15. (b) Thummel, R. P. Wett, 1992, 1
16. (c) Strekowski, L.; Czarny, A.; Lee, H. J. Fluor. Chem., 2000, 104, 281
17. (d) Suzuki, M.; Iwasaki, H.; Fujikawa, Y.; Kitahara, M.; Sakashita, M.; Sakoda, R. Bioorg. Med. Chem., 2001, 9, 2727
18. (e) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett., 2003, 44, 255
19. (f) Yadav, J. S.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. R. Tetrahedron Lett., 2005, 46, 7249
20. (g) Wang, G.-W.; Jia, C.-S.; Dong, Y.-W. Tetrahedon Lett., 2006, 47, 1059.
21. (a) McNaughton, B. R.; Miller, B. L. Org. Leff., 2003, 5, 4257
22. (b) Yadav, J. S.; Reddy, B. V. S.; Premalatha, K, Synlett, 2004, 963
23. (c) Wang, J.; Fan, X.; Zhang, X.; Han, L. Can. J. Chem., 2004, 82, 1192
24. (d) Arumugam, P.; Karthikeyan, G.; Atchudan, R.; Muralidharan, D.; Perumal, P. T. Chem. Lett., 2005, 34, 314
25. (e) De, S. K.; Gibbs, R. A. Tetrahedron Lea., 2005, 46, 1647
26. (f) Wu, J.; Zhang, L.; Diao, T.-N. Synlett, 2005, 2653.
27. (a) Arcadi, A.; Chiarini, M.; Giuseppe, S. D.; Marinelli, F. Synlett, 2003, 203
28. (b) Mogilaiah, K.; Reddy, C. S. Synth. Commun., 2003, 33, 3131
29. (c) Yadav, J. S.; Reddy, B. V. S.; Sreedhar, P.; Rao, R. S.; Nagaiah, K. Synthesis, 2004, 2381.
30. Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem., 2003, 68, 9371.
31. Jia, C.-S.; Zhang, Z.; Tu, S.-J.; Wang, G.-W. Org. Biomol. Chem., 2006, 4, 104.
32. (a) Zhang, Z.; Dong, Y.-W.; Wang, G.-W.; Komatsu, K. Synlett, 2004, 61
33. (b) Zhang, Z.; Dong, Y.-W.; Wang, G.-W.; Komatsu, K. Chem. Lett., 2004, 33, 168
34. (c) Zhang, Z.; Wang, G.-W.; Miao, C.-B.; Dong, Y.-W.; Shen, Y.-B. Chem. Commun., 2004, 1832
35. (d) Zhang, Z.; Gao, J.; Xia, J.-J.; Wang, G.-W. Org. Biomol. Chem., 2005, 3 , 1617.
36. 4, concentrated in vacuo and purified by column chromatography on silica gel with petroleum ether-EtOAc (9:1) as an eluent to afford the pure quinoline.