Solvent-free microwave-assisted synthesis of new 2-Aryl- Tetrahydroquinolines using three-component povarov reaction

Letters in Organic Chemistry

Volumn 6, Issue 3, 2009, Pages 208-212

  Astudillo, Luis S ^a   Margarita, Gutiérrez C ^a   Gaete, Hugo ^a   Kouznetsov, Vladimir V ^b   Meléndez, Carlos M ^b   Palenzuela, J Antonio ^c   Gabriel, Vallejos G ^d  

^a UNIVERSIDAD DE TALCA   (Chile)

^b UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

^d UNIVERSIDAD AUSTRAL DE CHILE   (Chile)

Author keywords

2 Aryl 1, 2, 3, 4 tetrahydroquinolines; Dry media; Microwave heated three component Povarov (imino Diels Alder) reaction

Indexed keywords

EID: 69249229770     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809787893145     Document Type: Article

References (30)

1. Keck, D.; Vanderheiden, S.; Bräse S. Eur. J. Org. Chem., 2006, 4916.
2. Fisher, M. J.; Backer, R. T.; Husain, S.; Hsiung, H. M.; Mullaney, J. T.; O'Brian, T. P.; Ornstein, P. L.; Rothhaar, R. R.; Zgombick, J. M.; Briner, K. Bioorg. Med. Chem. Lett., 2005, 15, 4459.
3. Singer, J. M.; Barr, B. M.; Coughenour, L. L.; Gregory, T. F.; Walters, M. A. Bioorg. Med. Chem. Lett., 2005, 15, 4560.
4. Guo, T.; Gu, H.; Hobbs, D. W.; Rokosz, L. L.; Stauffer, T. M.; Jacob, B.; Clader, J. W. Bioorg. Med. Chem. Lett., 2007, 17, 3010.
5. Chen, W.; Lin, Z.; Ning, M.; Yang, C.; Yan, X.; Xie, Y.; Shen, X.; Wang, M.-W. Bioorg. Med. Chem. Lett., 2007, 15, 5828.
6. Eastman, R. T.; White, J.; Hucke, O.; Yokoyama, K.; Verlinde, C. L. M. J.; Hast, M. A.; Beese, L. S.; Gelb, M.H.; Rathod, P. K.; Van Voorhis, W. C. Mol. Biochem. Parasitol., 2007, 152, 66.
7. Fisher, M. J.; Backer, R. T.; Husain, S.; Hsiung, H. M.; Mullaney, J. T.; ÓBrian, T. P.; Ornstein, P. L.; Rothhaar, R. R.; Zgombick, J. M.; Briner, K. Bioorg. Med. Chem. Lett., 2005, 15, 4459.
8. Guo, T.; Gu, H.; Hobbs, D. W.; Rokosz, L. L.; Stauffer, T. M.; Jacoba, B.; Claderb, J. W. Bioorg. Med. Chem. Lett., 2007, 17, 3010.
9. Chen, W.; Lin, Z.; Ning, M.; Yang, C.; Yan, X.; Xie, Y.; Shena, X.; Wang, M.-W. Bioorg. Med. Chem., 2007, 15, 5828.
10. See reviews: Katritzky, A.R.; Rachwal, S.; Rachwal, B. Tetrahedron, 1996, 52, 15031.
11. Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem., 1998, 35, 761.
12. Povarov, L. S. Russ. Chem. Rev., 1967, 36, 656.
13. Buonora, P.; Olsen, J.-C., Oh, T. Tetrahedron, 2001, 57, 6099.
14. Stevenson, P.; Graham, I. Arkivok, 2003 (vii), 139.
15. Beifuss, U.; Ledderhose, S.; Ondrus, V. Arkivoc, 2005, (v), 147.
16. Hermitage, S.; Jay, D. A.; Whiting, A. Tetrahedron Lett., 2002, 9633.
17. Hermitage, S.; Howard, J. A. K.; Jay, D. A.; Pritchard, R. G.; Probert, M. R.; Whiting, A. Org. Biomol. Chem., 2004, 2, 2451.
18. Kouznetsov, V. V.; Astudillo, S.L., Vargas, M.L.Y.; Cazar, R.M.E. J. Chil. Chem. Soc., 2004, 107.
19. Kouznetsov, V. V.; Romero, A. R.; Astudillo, L.; Fierro, R. Mol. Divers., 2006, 10, 29.
20. Kouznetsov, V. V.; Zubkov, F.I.; Mora, U.; Voskressensky, L.G.; Vargas, M.L.Y.; Astudillo, S.L.; Stashenko, E.E. Lett. Org. Chem., 2004, 1, 37.
21. Khan, K. M.; Zia-Ullah; Rani, M.; Perveen, S.; Haider, S.M.; Choudhary, M.I.; Rahman, A-U.; Voelter, W. Lett. Org. Chem., 2004, 1, 50.
22. See reviews:Dallinger, D.; Kappe, C. O. Chem. Rev., 2007, 107, 2563.
23. De la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev., 2005, 34, 164.
24. Yang, H.J.; Sun, W.H.; Li, Z.L.; Ma, Z. Chin. Chem. Lett., 2002, 13, 3.
25. Neves, F.R.; De Oliveira, R.; Srivastava, R. J. Braz. Chem. Soc., 2007, 18, 1410.
26. Xing, X.; Wu, J.; Dai, W.-M. Tetrahedron, 2006, 62, 11200.
27. Katrizky, A. R.; Rachwal, B.; Rachwal, S. J. Org. Chem., 1995, 60, 3993.
28. Hadden, M.; Nieuwenhuyezen, M.; Potts, D.; Stevenson, P. J.; Thompson, N. Tetrahedron, 2001, 57, 5615.
29. To accelerate the reaction time, the reaction mixture was heated (2- 5 h). However, TLC analysis indicated at the formation of complex product mixture.
30. Zhang, T.; Jin, H. J. Int. J. Environ. Pollut., 2001, 15, 568.