Sequential catalytic process: synthesis of quinoline derivatives by AuCl3/CuBr-catalyzed three-component reaction of aldehydes, amines, and alkynes

Tetrahedron

Volumn 64, Issue 12, 2008, Pages 2755-2761

  Xiao, Fengping ^a   Chen, Yulin ^a   Liu, Yu ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Alkyne; Catalysis; Gold; Nucleophilic addition; Propargyl amine; Quinoline

Indexed keywords

2 (3 BROMOPHENYL) 4 PHENYLQUINOLINE; 2 (3 BROMOPHENYL) 6 METHYL 4 PHENYLQUINOLINE; 2 (3 METHOXYPHENYL) 4 PHENYLQUINOLINE; 2 (4 BROMOPHENYL) 4 PHENYLQUINOLINE; 2 (4 PHENYLPHENYL) 4 PHENYLQUINOLINE; 2 [2 (ALLYLOXY)PHENYL] 6 METHYL 4 PHENYLQUINOLINE; 4 (NAPHTHALEN 1 YL) 2 PHENYLQUINOLINE; 4 PHENYL 2 (2 TOLYL)QUINOLINE; 6 METHYL 4 METHYL 2 (2 TOLYL)QUINOLINE; ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; AMINE; BROMIDE; COPPER; COPPER BROMIDE; GOLD CHLORIDE; IMINE; N [1 PHENYL 5 (TETRAHYDRO 2H PYRAN 2 YLOXY)PENT 2 YNYL]BENZENAMINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 39149087343     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.046     Document Type: Article

References (66)

1. For recent reviews, see:
2. Aubert C., Buisine O., and Malacria M. Chem. Rev. 102 (2002) 813
3. Méndez M., and Echavarren A.M. Eur. J. Org. Chem. (2002) 15
4. Hashmi A.S.K. Gold Bull. 36 (2003) 3
5. Lloyd-Jones G.C. Org. Biomol. Chem. 1 (2003) 215
6. Miki K., Uemura S., and Ohe K. Chem. Lett. (2005) 1068
7. Echavarren A.M., and Nevado C. Chem. Soc. Rev. 33 (2004) 431
8. Bruneau C. Angew. Chem., Int. Ed. 44 (2005) 2328
9. Hashmi A.S.K. Angew. Chem., Int. Ed. 44 (2005) 6990
10. Hoffmann-Röder A., and Krause N. Org. Biomol. Chem. 3 (2005) 387
11. Ma S., Yu S., and Gu Z. Angew. Chem., Int. Ed. 45 (2006) 200
12. Fukuda Y., and Utimoto K. J. Org. Chem. 56 (1991) 3729
13. Teles J.H., Brode S., and Chabanas M. Angew. Chem., Int. Ed. 37 (1998) 1415
14. Mizushima E., Sato K., Hayashi T., and Tanaka M. Angew. Chem., Int. Ed. 41 (2002) 4563
15. Casado R., Contel M., Laguna M., Romero P., and Sanz S. J. Am. Chem. Soc. 125 (2003) 11925
16. Roembke P., Schmidbaur H., Croje S., and Raubenheimer H. J. Mol. Catal. A 212 (2004) 35
17. Liu Y., Song F., Song Z., Liu M., and Yan B. Org. Lett. 7 (2005) 5409
18. Antoniotti S., Genin E., Michelet V., and Gênet J.-P. J. Am. Chem. Soc. 127 (2005) 9976
19. Fukuda Y., and Utimoto K. Synthesis (1991) 975
20. Arcadi A., DiGiuseppe S., Marinelli F., and Rossi E. Adv. Synth. Catal. 343 (2001) 443
21. Gorin D.J., Davis N.R., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 11260
22. For selected recent developments, see:
23. Hashmi A.S.K., Frost T.M., and Bats J.W. J. Am. Chem. Soc. 122 (2000) 11553
24. Nieto-Oberhuber C., Muñoz M.P., Buñuel E., Nevado C., Cárdenas D.J., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 2402
25. Kennedy-Smith J.J., Staben S.T., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 4526
26. Mamane V., Gress T., Krause H., and Fürstner A. J. Am. Chem. Soc. 126 (2004) 8654
27. Staben S.T., Kennedy-Smith J.J., and Toste F.D. Angew. Chem., Int. Ed. 43 (2004) 5350
28. Luzung M.R., Markham J.P., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 10858
29. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 11806
30. Sherry B.D., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 15978
31. Nieto-Oberhuber C., Lopez S., and Echavarren A.M. J. Am. Chem. Soc. 127 (2005) 6178
32. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 127 (2005) 6962
33. Gagosz F. Org. Lett. 7 (2005) 4129
34. Genin E., Toullec P.Y., Antoniotti S., Brancour C., Genêt J.-P., and Michelet V. J. Am. Chem. Soc. 128 (2006) 3112
35. Hashmi A.S.K., Schwarz L., Choi J.-H., and Frost T.M. Angew. Chem., Int. Ed. 39 (2000) 2285
36. Asao N., Takahashi K., Lee S., Kasahara T., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 12650
37. Asao N., Aikawa H., and Yamamoto Y. J. Am. Chem. Soc. 126 (2004) 7458
38. Yao T., Zhang X., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 1164
39. Kim N., Kim Y., Park W., Sung D., Gupta A.K., and Oh C.H. Org. Lett. 7 (2005) 5289
40. Yao X.Q., and Li C.-J. Org. Lett. 8 (2006) 1953
41. Buzas A., Istrate F., and Gagosz F. Org. Lett. 8 (2006) 1957
42. Morita N., and Krause N. Angew. Chem., Int. Ed. 45 (2006) 1897
43. Reetz M.T., and Sommer K. Eur. J. Org. Chem. (2003) 3485
44. Mamane V., Hannen P., and Fürstner A. Chem.-Eur. J. 10 (2004) 4556
45. Nevado C., and Echavarren A.M. Chem.-Eur. J. 11 (2005) 3155
46. Wei C., Li Z., and Li C.-J. Synlett (2004) 1472
47. Wei C., Li Z., and Li C.-J. Org. Lett. 5 (2003) 4473
48. Li Z., Wei C., Chen L., Varma R.S., and Li C.-J. Tetrahedron Lett. 45 (2004) 2443
49. Li C.-J., and Wei C. Chem. Commun. (2002) 268
50. Wei C., and Li C.-J. J. Am. Chem. Soc. 124 (2002) 5638
51. Commermann N., Koradin C., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 42 (2003) 5763
52. Shi L., Tu Y.-Q., Wang M., Zhang F.-M., and Fan C.-A. Org. Lett. 6 (2004) 1001
53. Li Z., and Li C.-J. J. Am. Chem. Soc. 126 (2004) 11810
54. Choudary B.M., Sridhar C., Kantam M.L., and Sreedhar B. Tetrahedron Lett. 45 (2004) 7319
55. Bieber L.W., and Silva M.F. Tetrahedron Lett. 45 (2004) 8281
56. Benaglia M., Negri D., and Dell'Anna G. Tetrahedron Lett. 45 (2004) 8705
57. Black D.A., and Arndtsen B.A. Org. Lett. 6 (2004) 1107
58. Wei C., and Li C.-J. J. Am. Chem. Soc. 125 (2003) 9584
59. For a recent review, see:. Ajamian A., and Gleason J.L. Angew. Chem., Int. Ed. 43 (2004) 3754
60. Li Z., Zhang J., Brouwer C., Yang C.-G., Reich N.W., and He C. Org. Lett. 8 (2006) 4175
61. Rosenfeld D.C., Shekhar S., Takemiya A., Utsunomiya M., and Hartwig J.F. Org. Lett. 8 (2006) 4179
62. Damavandi J.A., Zolfigol M.A., and Karami B. Synth. Commun. 31 (2001) 3183
63. Forrest T.P., Douphinee G.A., and Deraniyagala S.A. Can. J. Chem. 63 (1985) 412
64. Bohlmann F. Chem. Ber. 85 (1952) 390
65. Rudler H., Alvarez C., Denise B., Parlier A., and Vaissermann J. J. Organomet. Chem. 684 (2003) 105
66. Sun J., and Kozmin S.A. J. Am. Chem. Soc. 127 (2005) 13512