An efficient synthesis of new C-2 aryl substituted quinolines based on three component imino Diels-Alder reaction

Molecular Diversity

Volumn 10, Issue 1, 2006, Pages 29-37

  Kouznetsov, Vladimir V ^a   Romero Bohórquez, Arnold R ^a   Saavedra, Luis Astudillo ^b   Medina, Ricardo Fierro ^c  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD DE TALCA   (Chile)

^c Laboratorio de Síntesis Orgánica Y Organometálicos   (Colombia)

Author keywords

C 2 substituted quinolines; Three component imino Diels Alder reaction

Indexed keywords

PYRROLIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; DIELS ALDER REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

CYCLIZATION; IMINES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM;

EID: 30744468567     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-006-2344-8     Document Type: Article

References (20)

1. Kouznetsov, V.V., Vargas Méndez, L.Y. and Meléndez Gómez, C.M., Recent progress in the synthesis of quinolines, Curr. Org. Chem., 9 (2005) 141-161.
2. Cho, C.S., Kim, B.T., Choi, H.J., Kim, T.J. and Shim, S.C., Ruthenium-Catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines, Tetrahedron, 59 (2003) 7997-8002.
3. Reviews: (a) Povarov, L.S. Russ. Chem. Rev., 36 (1967) 656-670;
4. (b) Boger, D.L., Weinreb, S.M., Hetero diels-alder methodology in organic synthesis, Academic Press, San Diego, 1987.
5. (c) Weinreb, S.M., XXX, In Trost, B.M. and Fleming, I. (Eds.), Comprehensive Organic Synthesis, Vol. 5: Pergmon, Oxford, 1991, pp. 401-449.
6. Some recent works: (a) Kouznetsov, V.V., Zubkov, F.I., Mora Cruz, U., Voskressensky, L.G., Vargas Mendez, L.Y., Astudillo L. and Stashenko, E.E., An efficient synthesis of hexahydro oxaisoindolo[2,1-a]quinoline derivatives via the Diels-Alder reactions, Lett. Org. Chem., 1 (2004) 37-39;
7. (b) Fadel, F., Titouni, S.L., Soufioui, M., Ajamay, H. and Mazzah, A., Synthèse de nouveaux dérivés té trahydroquinoléines et quinoléines via la réaction d'aza-Diels-Alder suivie d'aromatisation, Tetrahedron Lett., 45 (2004) 5905-5908.
8. (a) Kobayashi, S. and Nagayama, S., A New methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polimer-supported scandium catalyst, J. Am. Chem. Soc., 118 (1996) 8977-8978;
9. 3, Tetrahedron, 54 (1998) 5089-5096;
10. (c) Kiselyov, A., Smith, L., Virgilio, A., and Armstrong, R., Immobilized aldehydes and olefins in the solid support synthesis of tetrahydroquinolines via a three component condensation, Tetrahedron, 54 (1998) 7987-7996.
11. 3-N-Aryl-aldimine and vinyl ethers, Tetrahedron Lett., 39 (1998) 5765-5768.
12. (a) Katritzky, A; Rachwal, B. and Rachwal, S., Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)- tetrahydroquinolines, J. Org. Chem., 60 (1995) 3993-4001;
13. (b) Talukdar, S., Chen, C-T. and Fang, J-M., A stereoselective route to polysubstituted tetrahydroquinolines by benzotriazole-promoted condensation of aliphatic aldehydes and aromatic amines, J. Org. Chem., 65 (2000) 3148-3153;
14. (c) Zhang, W., Guo, Y., Liu, Z., Jin, X., Yang, L. and Liu, Z.-L., Photochemically catalyzed Diels-Alder reaction of arylimines with N-Vinylpyrrolidinone and N-vinylcarbazole by 2,4,6-triphenylpyrylium salt: Synthesis of 4-heterocycle-substituted tetrahydroquinoline derivatives, Tetrahedron 61 (2005) 1325-1333.
15. Demaude, T., Knerr, L. and Pasau, P., New synthetic pathway to diverse 2-substituted quinolines based on a multicomponent reaction: Solution-phase and solid-phase applications, J. Comb. Chem., 6 (2004) 768-775.
16. (a) Urbina, J.M.G., Cortés, J.C., Palma, A., López, S.N., Zacchino, S.A., Enriz, D.R., Ribas, J.C. and Kouznetsov, V., Inhibitors of the Fungal Cell Wall. Synthesis of 4-Aryl-4-N-arylamine-1-butenes and Related Compounds with Inhibitory Activities on β (1-3) Glucan and Chitin Synthases, Bioorg. Med. Chem., 8 (2000) 691-698;
17. (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. and Zacchino S.A., In Vitro Antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers, Bioorg. Med. Chem., 11 (2003) 1531-1550;
18. (c) Villagra, S.E., Bernini, M.C., Rodríguez, A.M., Zacchino, S.A., Kouznetsov, V.V. and Enriz, R.D., Conformational and electronic study of homoallylamines with inhibitory properties against polymers of fungal cell wall, J. Mol. Structure (Theochem), 666-667 (2003) 587-598.
19. Kouznetsov, V.V., Astudillo Saavedra, L., Vargas Méndez, L.Y. and Cazar Ramírez, M.E., Synthesis of some secondary amine derivatives bearing a heteroaryl fragment, J. Chil. Chem. Soc., 49 (2004) 107-203.
20. Roberts, R., An introduction to modern experimental organic chemistry. New York: Ed. Holt, Rinehardt and Winston (1969).