Transformation of 2-(α-furyl)-4-(2-oxopyrrolidinyl-1)-1,2,3,4-tetrahydroquinolines, cycloadducts of the imino Diels-Alder reaction: A simple synthesis of new quinoline derivatives

Letters in Organic Chemistry

Volumn 3, Issue 9, 2006, Pages 699-702

  Kouznetsov, Vladímir V ^a   Cruz, Uriel Mora ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

Author keywords

C 2 furyl substituted quinolines; Imino Diels Alder cycloaddition; Intramolecular Diels Alder with furan; Isoindolo 2,1 a quinolines; Oxaisoindolo 2,1 a quinolines

Indexed keywords

EID: 33750440516     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806778700042     Document Type: Article

References (31)

1. Katritzky, A.R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
2. Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761.
3. Kouznetsov, V.V.; Vargas Méndez, L.Y.; Meléndez Gómez, C.M. Curr. Org. Chem. 2005, 9, 141.
4. (a) Cho, C.S.; Kim, B.T.; Choi, H.J.; Kim, T.-J.; Shim, S.C. Tetrahedron 2003, 59, 7997;
5. (b) Cho, C. S.; Kim, B.T.; Kim, T.J.; Shim, S.C. Chem. Commun. 2001, 2576.
6. (a) Povarov, L.S. Russ. Chem. Rev. 1967, 36, 656;
7. (b) Boger, D.L.; Weinreb, S.M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987;
8. (c) Weinreb, S.M. In Comprehensive Organic Synthesis, Trost, B.M., Fleming, I. Eds.: Pergmon, Oxford, 1991; Vol. 5, pp. 401-449.
9. (a) Kobayashi, S.; Nagayama, S.A. J. Am. Chem. Soc. 1996, 118, 8977;
10. (b) Kiselyov, A.; Smith, L.; Armstrong, R. Tetrahedron 1998, 54, 5089;
11. (c) Kiselyov, A.; Smith, L.; Virgilio, A.; Armstrong, R. Tetrahedron 1998, 54, 7987.
12. (a) Crousse, B.; Bèguè, J-P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 5765;
13. (b) Crousse, B.; Bèguè, J-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009;
14. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
15. (a) Zhang, W.; Guo, Y.; Liu, Z.; Jin, X.; Yang, L.; Liu, Z.-L. Tetrahedron 2005, 61, 1325;
16. (b) Han, B.; Jia, X-D.; Jin, X.-L.; Zhou, Y.-L.; Yang, L.; Liu, Z.-L.; Yu, W. Tetrahedron Lett. 2006, 47, 3545;
17. (c) Kouznetsov, V.V.; Bohórquez Romero, A.R.; Astudillo Saavedra, L.; Fierro Medina, R. Molecular Diversity 2006, 10, 29;
18. (d) Kouznetsov, V.V.; Astudillo Saavedra, L.; Vargas Méndez, L.Y.; Cazar Ramírez, M.E. J. Chil. Chem. Soc. 2004, 49, 319.
19. Demaude, T.; Knerr, L.; Pasau, P. J. Comb. Chem. 2004, 6, 768.
20. (a) Ghelfi, F.; Parsons, A.F.; Tommasini D.; Mucci, A. Eur. J. Org. Chem. 2001, 1845;
21. (b) Paulivann, K.; Jacobs, J.W. Tetrahedron 1999, 55, 7433;
22. (c) Paulivann, K.; Chen, T.; Jacobs, J.W. Synlett 1999, 1609.
23. (a) Kametani, T.; Takeda, H.; Suzuki, Y.; Rasai, R.; Honda, T. Heterocycles 1986, 24, 3385;
24. (b) Savitha, G.; Perumal, P.T. Tetrahedron Lett. 2006, 47, 3589;
25. (c) Kouznetsov, V.V.; Zubkov, F.I.; Mora Cruz, U.; Voskressensky, L.G.; Vargas Méndez, L.Y.; Astudillo, L.; Stashenko, E.E. Lett. Org. Chem. 2004, 1, 37.
26. (a) Urbina, J.M.G.; Cortés, J.C.; Palma, A.; López, S.N.; Zacchino, S.A.; Enriz, D.R.; Ribas, J.C.; Kouznetsov, V. Bioorg. Med. Chem. 2000, 8, 691;
27. (b) Vargas, M.L.Y.; Castelli, M.V.; Kouznetsov, V.V.; Urbina, G.J.M.; López, S.N.; Sortino, M.; Enriz, R.D.; Ribas, J.C.; Zacchino, S.A. Bioorg. Med. Chem. 2003, 11, 1531;
28. (c) Kouznetsov, V.V.; Vargas Méndez, L.Y.; Tibaduiza, B.; Ochoa, C.; Montero, Pereira, D.; Nogal Ruiz, J.J.; Portillo, C.F.; Gómez, A.B.; Bahsas, A.; Amaro-Luis, J.M. Arch. Pharm. 2004, 337, 127.
29. 3): δ = 18.2, 30.7, 31.2, 42.2, 47.5, 49.6, 105.7, 110.3, 116.4, 120.6, 123.2, 126.3, 128.3, 142.1, 143.6, 154.6, 175.8.
30. 3): δ = 55.5, 105.3, 109.1, 112.1, 117.8, 122.4, 128.1, 130.8, 135.3, 143.6, 144.1, 146.9, 153.8, 157.6.
31. 3): δ = 14.2, 18.1, 31.0, 42.3, 47.8, 58.0, 60.3, 121.9, 124.4, 125.5, 126.5, 128.6, 129.0, 129.7, 132.0, 132.5, 135.3, 143.4, 165.8, 175.8.