Palladium-assisted multicomponent synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino[1,8]naphthyridines

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6454-6460

  Abbiati, Giorgio ^a   Arcadi, Antonio ^b   Canevari, Valentina ^a   Capezzuto, Luca ^a   Rossi, Elisabetta ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; CARBON MONOXIDE; CATALYSIS; IODINE COMPOUNDS; PALLADIUM; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SUBSTRATES; SYNTHESIS (CHEMICAL);

ARYL IODIDES; MULTICOMPONENT SYNTHESIS; PHOSPHINES; PRIMARY AMINES;

PROTEINS;

4 AMINO[1,8]NAPHTHYRIDINE DERIVATIVE; 4 AMINOQUINOLINE DERIVATIVE; AMINE; AROMATIC AMINE; CARBON MONOXIDE; IODIDE; NAPHTHYRIDINE DERIVATIVE; PALLADIUM; PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL COMPOSITION; CHEMICAL REACTION; SYNTHESIS;

EID: 23044508811     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050882q     Document Type: Article

References (54)

1. Clark, J.; Macquarrie, D. In Handbook of Green Chemistry & Technology; Blackwell Science Ltd.: Oxford, 2002.
2. For recent reviews, see: (a) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
3. (b) Bienaymé, H.; Hulme, C.; Tuch, A.; Walle, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH Verlag: Weinheim, 2002.
4. (c) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
5. (d) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
6. (a) Nishimura, T.; Uemura, S. Synlett 2004, 201-216.
7. (b) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101-4111.
8. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002.
9. (a) Arcadi, A.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. Adv. Synth. Catal. 2001, 343, 443-446.
10. (b) Arcadi, A.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. Tetrahedron: Asymmetry 2001, 12, 2715-2720.
11. (c) Rossi, E.; Arcadi, A.; Abbiati, G.; Attanasi, O. A.; De Crescentini, L. Angew. Chem., Int. Ed. 2002, 41, 1400-1402.
12. (d) Abbiati, G.; Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. J. Org. Chem. 2003, 68, 6959-6966.
13. (e) Abbiati, G.; Arcadi, A.; Bellinazzi, A.; Beccalli, E.; Rossi, E.; Zanzola, S. J. Org. Chem. 2005, 70, 4088-4095.
14. (a) Arcadi, A.; Rossi, E.; Marinelli, F. Tetrahedron 1999, 55, 13233-13250.
15. (b) Abbiati, G.; Beccalli, E.; Marchesini, A.; Rossi, E. Synthesis 2001, 2477-2483.
16. (c) Abbiati, G.; Arcadi, A.; Marinelli, F.; Rossi, E. Tetrahedron Lett. 2001, 42, 3705-3708.
17. (d) Abbiati, G.; Arcadi, A.; Marinelli, F.; Rossi, E. Synthesis 2002, 1912-1916.
18. (e) Abbiati, G.; Arcadi, A.; Marinelli, F.; Rossi, E. Eur. J. Org. Chem. 2003, 1423-1427.
19. (f) Abbiati, G.; Beccalli, E.; Arcadi, A.; Rossi, E. Tetrahedron Lett. 2003, 44, 5331-5334.
20. Rossi, E.; Abbiati, G.; Canevari, V.; Nava, D.; Arcadi, A. Tetrahedron 2004, 60, 11391-11398.
21. Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1999, 401-404.
22. Torii, S.; He Xu, L.; Sadakane, M.; Okumoto, H. Synlett 1992, 513-514.
23. (a) Torii, S.; Okumoto, H.; He Xu, L.; Sadakane, M.; Shostakovsky, M. V.; Ponomaryov, A. B.; Kalinin, V. N. Tetrahedron 1993, 49, 6773-6784.
24. (b) Kalinin, V. N.; Shostakovsky, M. V.; Ponomaryov, A. B. Tetrahedron Lett. 1992, 33, 373-376.
25. (c) Kalinin, V. N.; Shostakovsky, M. V.; Ponomaryov, A. B. Tetrahedron Lett. 1990, 31, 4073-4076.
26. (a) Arcadi, A.; Rossi, E. Tetrahedron Lett. 1996, 37, 6811-6814.
27. (b) Delaude, L.; Masdeu, A. M.; Alper, H. Synthesis 1994, 1149-1151.
28. (c) Brocato, E.; Castagnoli, C.; Catellani, M.; Chiusoli, G. P. Tetrahedron Lett. 1992, 33, 7433-7436.
29. (d) An, Z.; Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1990, 397, C31-32.
30. (e) Tamaru, Y.; Ochiai, H.; Yoshida, Z.-i. Tetrahedron Lett. 1984, 25, 3861-3864.
31. (f) Kobayashi, T.; Tanaka, M. J. Chem. Soc. Chem. Commun. 1981, 333-334.
32. (a) Negishi, E.-i. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 2, Chapter VI.1, p 2309.
33. (b) Tamaru, Y.; Kimura, M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 2, Chapter VI.2.2, Section I, p 2447.
34. (a) Mori, M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 2, Chapter VI.2, Section B, pp 2314-2322.
35. (b) Huang, L.; Ozawa, F.; Yamamoto, A. Organometallics 1990, 9, 2603-2611.
36. (c) Ozawa, F.; Soyama, H.; Yamamoto, T.; Yamamoto, A. J. Am. Chem. Soc. 1985, 107, 3235-3245.
37. Hu, Y.; Zhang, Y.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368 and references therein.
38. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2770.
39. Ozawa, S.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640-1651.
40. (a) Tsuji, J. Transition Metal Reagents and Catalysts. In Innovation in Organic Synthesis; Wiley: New York, 2000; Chapter 2.2.2, p 14.
41. (b) Lee, J. S.; Lee, S. M.; Kim, K. D.; Cho, N. S.; Oh, J. S. J. Mol. Catal. 1993, 81, 17-25.
42. Choueiry, D.; Negishi, E.-i. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 1, Chapter II.2, p 41.
43. (a) Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997-1030.
44. (b) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
45. (c) Amatore, C.; Jutand, A.; Meyer, G.; Atmani, H.; Khalil, F.; Chahdi, F. O. Organometallics 1998, 17, 2958-2964.
46. (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, M. L. Tetrahedron 2003, 59, 4661-4671.
47. (b) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406.
48. Negishi, E.-i. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 1, Chapter I.2, Section C, p 31.
49. (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
50. (b) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12670-12671.
51. (c) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704.
52. Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
53. Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349-3352.
54. Asao, N.; Nogami, T.; Takanashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764-765.