Electrophile-driven regioselective synthesis of functionalized quinolines

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2598-2601

  Ali, Shaukat ^a   Zhu, Hai Tao ^a   Xia, Xiao Feng ^a   Ji, Ke Gong ^a   Yang, Yan Fang ^a   Song, Xian Rong ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IODINATED HYDROCARBON; IODINE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; HYDROCARBONS, IODINATED; IODINE; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM;

EID: 79956111834     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2007154     Document Type: Article

References (91)

1. Kouznetsov, V. V.; Vargas Méndez, L. Y.; Meléndez Gómez, C. M. Curr. Org. Chem. 2005, 9, 141-161
2. Newhouse, B. J.; Bordner, J.; Augeri, D. J.; Litts, C. S.; Kleinman, E. F. J. Org. Chem. 1992, 57, 6991
3. Torii, S.; Xu, L. H.; Sadakane, M.; Okumoto, H. Synlett 1992, 513
4. Nobuhide, M.; Yoshinobu, Y.; Hiroshi, I.; Yoshio, O.; Tamejiro, H. Tetrahedron Lett. 1993, 24, 8263
5. Croisey-Delcey, M.; Croisy, A.; Carrez, D.; Huel, C.; Chiaroni, A.; Ducrot, P.; Bisagni, E.; Jin, L.; Leclercq, G. Bioorg. Med. Chem. 2000, 8, 2629
6. Manske, R. H. F.; Kukla, M. Org. React. 1953, 7, 59
7. Bergstrom, F. W. Chem. Rev. 1944, 35, 153
8. Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37
9. Jones, G. In The Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; John Wiley and Sons: Chichester, UK, 1977; Vol. 32, Part I, pp 93-318.
10. Reitsema, R. H. Chem. Rev. 1948, 43, 47
11. Bergstrom, F. W. Chem. Rev. 1944, 35, 156
12. For selected papers, see: Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926
13. Horn, J.; Marsden, S. P.; Nelson, A.; House, D.; Weingarten, G. G. Org. Lett. 2008, 10, 4117
14. Arisawa, M.; Nishida, A.; Nakagawa, M. J. Organomet. Chem. 2006, 691, 5109
15. Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 4592
16. Liu, X.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2008, 47, 3805
17. For selected papers, see: Zhang, Z.; Tan, J.; Wang, Z. Org. Lett. 2008, 10, 173
18. Sakai, N.; Annaka, K.; Fujita, A.; Sato, A.; Konakahara, T. J. Org. Chem. 2008, 73, 4160
19. Arcadi, A.; Aschi, M.; Marinelli, F.; Verdecchia, M. Tetrahedron. 2008, 64, 5354
20. Li, L.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 10707
21. Gabriele, B.; Mancuso, R.; Salerno, G.; Ruffolo, G.; Plastina, P. J. Org. Chem. 2007, 72, 6873
22. Sakai, N.; Annaka, K.; Konakahara, T. J. Org. Chem. 2006, 71, 3653
23. Godet, T.; Belmont, P. Synlett 2008, 2513
24. Bi, H.-P.; Guo, L.-N.; Duan, X.-H.; Gou, F.-R.; Huang, S.-H.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2007, 9, 397
25. Xie, Y.-X.; Liu, X.-Y.; Wu, L.-Y.; Han, Y.; Zhao, L.-B.; Fan, M.-J.; Liang, Y.-M. Eur. J. Org. Chem. 2008, 1013
26. Wen, S.-G.; Liu, W.-M.; Liang, Y.-M. J. Org. Chem. 2008, 73, 4342
27. Xie, Y.-X.; Yan, Z.-Y.; Qian, B.; Deng, W.-Y.; Wu, L.-Y.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2009, 5451
28. Xie, Y.-X.; Yan, Z.-Y.; Wang, D.-Z.; Wu, L.-Y.; Qian, B.; Liu, X.-Y.; Liang, Y.-M. Eur. J. Org. Chem. 2009, 2283
29. Ji, K.-G.; Zhu, H.-T.; Yang, F.; Shu, X.-Z.; Zhao, S.-C.; Shaukat, A.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2010, 16, 1615
30. For early studies on the electrophilic cyclization reaction, see: Ren, X.-F.; Turos, E. Tetrahedron Lett. 1993, 34, 1575
31. Kitamura, T.; Takachi, T.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1992, 1, 1969
32. Kitamura, T.; Kobayashi, S.; Taniguchi, H.; Hori, K. J. Am. Chem. Soc. 1991, 113, 6240
33. Ten Hoedt, R. W. M.; Van Koten, G.; Noltes, J. G. Synth. Commun. 1977, 7, 61
34. Sonoda, T.; Kawakami, M.; Ikeda, T.; Kobayashi, S.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1976, 612
35. Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011
36. Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905
37. Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651
38. Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377
39. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432
40. Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141
41. Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207
42. Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin. Trans. 2001, 1, 2874
43. Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans. 2002, 1, 622
44. Bew, S. P.; Knight, D. W. Chem. Commun. 1996, 1007
45. Djuardi, E.; McNelis, E. Tetrahedron Lett. 1999, 40, 7193
46. Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769
47. Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679
48. Liu, Y.; Zhou, S. Org. Lett. 2005, 7, 4609
49. Bew, S. P.; El-Taeb, G. M. M.; Jones, S.; Knight, D. W.; Tan, W.-F. Eur. J. Org. Chem. 2007, 5759
50. Arimitsu, S.; Jacobsen, J. M.; Hammond, G. B. J. Org. Chem. 2008, 73, 2886
51. Huang, X.; Fu, W.; Miao, M. Tetrahedron Lett. 2008, 49, 2359
52. Mohapatra, D. K.; Das, P. P.; Pattanayak, M. R.; Yadav, J. S Chem.-Eur. J. 2010, 16, 2072
53. Mancuso, R.; Mehta, S.; Gabriele, B.; Salerno, G.; Jenks, W. S.; Larock, R. C. J. Org. Chem. 2010, 75, 897
54. Barluenga, J.; Trincado, M.; Rublio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406
55. Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539
56. Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037
57. Barluenga, J.; Vazque-Villa, H.; Ballesteros, A.; Gonzalez, J. M. J. Am. Chem. Soc. 2003, 125, 9028
58. Yue, D.; Della Ca, N.; Larock, R. C. Org. Lett. 2004, 6, 1581
59. Yao, T.; Larock, R. C. Tetrahedron Lett. 2002, 43, 7401
60. Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936
61. Oliver, M. A.; Gandour, R. D. J. Org. Chem. 1984, 49, 558
62. Biagetti, M.; Bellina, F.; Carpita, A.; Stabile, P.; Rossi, R. Tetrahedron 2002, 58, 5023
63. Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron 2003, 59, 2067
64. Huang, Q.; Hunter, J. A.; Larock, R. C. Org. Lett. 2001, 3, 2973
65. Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437
66. Barluenga, J.; Gonzalez, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1546
67. Huo, Z.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2010, 75, 1266
68. Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 15720
69. Ding, Q.; Wu, J. Adv. Synth. Catal. 2008, 350, 1850
70. Ding, Q.; Wang, Z.; Wu, J. J. Org. Chem. 2009, 74, 921
71. Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203
72. Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, W. J. Org. Lett. 2004, 6, 4391
73. Just, Z. W.; Larock, R. C. J. Org. Chem. 2008, 73, 2662
74. Crone, B.; Kirsch, S. F. J. Org. Chem. 2007, 72, 5435
75. Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409
76. Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 12230
77. Tang, B.-X.; Tang, D.-J.; Tang, S.; Yu, Q.-F.; Zhang, Y.-H.; Liang, Y.; Zhong, P.; Li, J.-H. Org. Lett. 2008, 10, 1063
78. Yao, T.; Yue, D.; Larock, R. C. J. Org. Chem. 2005, 70, 9985
79. Zhang, X.; Sarkar, S.; Larock, R. C. J. Org. Chem. 2006, 71, 236
80. Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121
81. Kothandaraman, P.; Rao, W.; Foo, S. J.; Philip Wai, H. C. Angew. Chem., Int. Ed. 2010, 49, 1-6
82. Hessian, K. O.; Flynn, B. L. Org. Lett. 2005, 8, 243-246
83. Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 5, pp 203-229.
84. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467
85. Suzuki, A. J. Organomet. Chem. 1999, 576, 147
86. Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145
87. Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; 49.
88. Miyaura, N. Chem. Rev. 1995, 95, 2457
89. Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427
90. Brase, S.; De Meijere, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 99.
91. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: San Diego, CA, 1985; pp 276-287.