A concise construction of polycyclic quinolines via annulation of ω-cyano-1-alkynes with diaryliodonium salts

Organic Letters

Volumn 15, Issue 18, 2013, Pages 4794-4797

  Wang, Yong ^a,b   Chen, Chao ^a   Zhang, Shu ^a,c   Lou, Zhenbang ^a,b   Su, Xiang ^a   Wen, Lirong ^b   Li, Ming ^b  

^a TSINGHUA UNIVERSITY   (China)

^b QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84884549972     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402164s     Document Type: Article

References (71)

1. Kaur, K.; Jain, M.; Reddy, R. P.; Jain, R. Eur. J. Med. Chem. 2010, 45, 3245
2. Reyes, F.; Fernández, R.; Urda, C.; Francesch, A.; Bueno, S.; de Eguilior, C.; Cuevas, C. Tetrahedron 2007, 63, 2432
3. Michael, J. P. Nat. Prod. Rep. 2008, 25, 166
4. Michael, J. P. Nat. Prod. Rep. 2007, 24, 223
5. Michael, J. P. Nat. Prod. Rep. 2005, 22, 627
6. Kouznetsov, V. V.; Vargas Méndez, L. Y.; Meléndez Gomez, C. M. Curr. Org. Chem 2005, 9, 141
7. Magomedov, N. A. Org. Lett. 2003, 5, 2509
8. Dzierzbicka, K.; Kolodziejczyk, A. M. J. Med. Chem. 2001, 44, 3606
9. Hubbs, J. L.; Heathcock, C. H. Org. Lett. 1999, 1, 1315
10. Gamage, S. A.; Spicer, J. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1999, 42, 2383
11. Inman, W. D.; O'Neill-Johnson, M.; Crews, P. J. Am. Chem. Soc. 1990, 112, 1
12. Gunawardana, G. P.; Kohmoto, S.; Gunasekara, S. P.; McConnell, O. J.; Koehn, F. E. J. Am. Chem. Soc. 1988, 110, 4856
13. Cain, B. F.; Atwell, G. J.; Denny, W. A. J. Med. Chem. 1975, 18, 1110
14. Sanders, J. M.; Clifford, D. P.; Lutz, R. E. J. Med. Chem. 1971, 14, 1126
15. Elks, J.; Ganellin, C. R. Dictionary of Drugs, 1 st ed.; Chapman and Hall: London, 1990; p 84.
16. Elks, J.; Ganellin, C. R. Dictionary of Drugs, 1 st ed.; Chapman and Hall: London, 1990; p 170.
17. Elks, J.; Ganellin, C. R. Dictionary of Drugs, 1 st ed.; Chapman and Hall: London, 1990; p 297.
18. Elks, J.; Ganellin, C. R. Dictionary of Drugs, 1 st ed.; Chapman and Hall: London, 1990; p 835.
19. Davis, K. L.; Powchick, P. Lancet 1995, 345, 625
20. Summers, W. K.; Majovski, L. V.; Marsh, G. M.; Tachiki, K.; Kling, A. N. Engl. J. Med. 1986, 315, 1241
21. Albert, A.; Gledhill, W. J. J. Soc. Chem. Ind. 1945, 64, 169
22. Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1997, 46, 541
23. Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1999, 51, 1883
24. Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Phytochemistry 2000, 53, 1075
25. Wall, M. E.; Wani, M. C. In Anticancer Agents Based on Natural Product Models; Cassadt, J. M.; Donuros, J. D., Eds.; Academic Press: New York, 1980; p 417.
26. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, J. A. J. Am. Chem. Soc. 1966, 88, 3888
27. Halim, R.; Aurelio, L.; Scammells, P. J.; Flynn, B. L. J. Org. Chem. 2013, 78, 4708
28. Hasaninejad, A.; Shekouhy, M.; Zare, A. Catal. Sci. Technol. 2012, 2, 201
29. Hasaninejad, A.; Zare, A.; Shekouhy, M.; Ameri-Rad, J. Green Chem. 2011, 13, 958
30. Tajik, H.; Niknam, K.; Sarrafan, M. Synth. Commun. 2011, 41, 2103
31. Piechowska, J.; Gryko, D. T. J. Org. Chem. 2011, 76, 10220
32. Barbero, M.; Bazzi, S.; Cadamuro, S.; Dughera, S. Tetrahedron Lett. 2010, 51, 2342
33. Yamuna, E.; Jayarampillai, K.; Prasad, R. J. Chem. Res 2010, 34, 385
34. Sridharan, V.; Ribelles, P.; Ramos, M. T.; Menendez, J. C. J. Org. Chem. 2009, 74, 5715
35. Yang, D.; Guo, W.; Cai, Y.; Jiang, L.; Jiang, K.; Wu, X. Heteroat. Chem. 2008, 19, 229
36. Some, S.; Ray, J. K. Tetrahedron Lett. 2007, 48, 5013
37. Khalilzadeh, M. A.; Hosseini, A.; Tajbakhsh, M. J. Heterocycl. Chem. 2007, 44, 535
38. Ma, Z.; Xiang, Z.; Luo, T.; Lu, K.; Xu, Z.; Chen, J.; Yang, Z. J. Comb. Chem. 2006, 8, 696
39. Basavaiah, D.; Rao, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 7379
40. Magomedov, N. A. Org. Lett. 2003, 5, 2509
41. Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765
42. Rossi, E.; Abbiati, G.; Arcadi, A.; Marinelli, F. Tetrahedron Lett. 2001, 42, 3705
43. Martins, M. A. P.; Frizzo, C. P.; Moreira, N. D.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140
44. Niementowski, S. J. Prakt. Chem. 1895, 51, 564
45. Bañón-Caballero, A.; Guillena, G.; Nájera, C. J. Org. Chem. 2013, 78, 5349
46. Shiri, M.; Zolgigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Adv. Heterocycl. Chem. 2011, 102, 139
47. Contelles, J. M.; Pérez-Mayoral, E.; Samadi, A.; Carreiras, M. C.; Soriano, E. Chem. Rev. 2009, 109, 2652
48. Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323
49. Su, X.; Chen, C.; Wang, Y.; Peng, J.; Lou, Z.; Li, M. Chem. Commun. 2013, 49, 6752
50. Peng, J.; Chen, C.; Wang, Y.; Lou, Z.; Li, M.; Xi, C.; Chen, H. Angew. Chem., Int. Ed. 2013, 52, 7574
51. Wang, F.; Chen, C.; Deng, G.; Xi, C. J. Org. Chem. 2012, 77, 4148
52. Yusubov, M. S.; Maskaev, A. V.; Zhdankin, V. V. ARKIVOC 2011, 370
53. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052
54. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
55. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523
56. Grushin, V. V. Chem. Soc. Rev. 2000, 29, 315
57. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123
58. Skucas, E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 134, 9090
59. Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610
60. Bielawski, M.; Olofsson, B. Chem. Commun. 2007, 2521
61. Olofsson, Bielawski, B. Org. Synth. 2009, 86, 308
62. Sargent, L. J.; Small, L. J. Org. Chem. 1946, 11, 359
63. Wang, Y.; Guan, X. L.; Wu, P. F.; Wang, C. M.; Cao, H.; Li, L.; Guo, X. J.; Wang, F.; Xie, N.; Jiang, F. C.; Chen, J. G. J. Med. Chem. 2012, 55, 3588
64. Szymanski, P.; Karpiński, A.; Mikiciuk-Olasik, E. Eur. J. Med. Chem. 2011, 46, 3250
65. Xu, H. H.; Wolf, C. Chem. Commun. 2009, 3035
66. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
67. Thomas, A. W.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 5400
68. Girgis, N. S.; Pedersen, E. B. Synthesis 1985, 5, 547
69. Sonogashira, K.; Tohda, Y.; Hagiwara, N. Tetrahedron Lett. 1975, 50, 4467
70. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
71. Miyaura, N.; Suzuki, A. Chem. Commun. 1979, 866