Visible-light-promoted and one-pot synthesis of phenanthridines and quinolines from aldehydes and o -Acyl hydroxylamine

Organic Letters

Volumn 17, Issue 11, 2015, Pages 2692-2695

  An, Xiao De ^a   Yu, Shouyun ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HETEROCYCLIC COMPOUND; HYDROXYLAMINE; OXIME; PHENANTHRIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; SYNTHESIS;

ALDEHYDES; AZA COMPOUNDS; CATALYSIS; HYDROXYLAMINES; LIGHT; MOLECULAR STRUCTURE; OXIMES; PHENANTHRIDINES; QUINOLINES;

EID: 84930943803     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01096     Document Type: Article

References (76)

1. Balasubramanian, M.; In Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, UK, 1996; Vol. 5, pp 245-300.
2. Prajapati, S. M.; Patel, K. D.; Vekariya, R. H.; Panchal, S. N.; Patel, H. D. RSC Adv. 2014, 4, 24463-24476
3. Dubost, E.; Dumas, N.; Fossey, C.; Magnelli, R.; Butt-Gueulle, S.; Ballandonne, C.; Caignard, D. H.; Dulin, F.; Sopkova de-Oliveira Santos, J.; Millet, P.; Charnay, Y.; Rault, S.; Cailly, T.; Fabis, F. J. Med. Chem. 2012, 55, 9693-9707
4. Jones, G. In Comprehensive Heterocyclic Chemistry; Pergamon Press: New York, 1984; Vol. 2, pp 395-510.
5. Marco-Contelles, J.; Pérez-Mayoral, E.; Samadi, A.; Carreiras, M. C.; Soriano, E. Chem. Rev. 2009, 109, 2652-2671
6. Kouznetsov, V. V. Tetrahedron 2009, 65, 2721-2750
7. Manske, R. H. Chem. Rev. 1942, 30, 113-144
8. West, A. P., Jr.; Van engen, D.; Pascal, R. A., Jr. J. Org. Chem. 1992, 57, 784-786
9. Marcos, A.; Pedregal, C.; Avendaño, C. Tetrahedron 1991, 47, 7459-7464
10. Gellerman, G.; Rudi, A.; Kashman, Y. Tetrahedron Lett. 1992, 33, 5577-5580
11. ONeill, P. M.; Storr, R. C.; Park, B. K. Tetrahedron 1998, 54, 4615-4622
12. Lysén, M.; Kristensen, J. L.; Vedsø, P.; Begtrup, M. Org. Lett. 2002, 4, 257-259
13. Chen, W.-L.; Chen, C.-Y.; Chen, Y.-F.; Hsieh, J.-C. Org. Lett. 2015, 17, 1613-1616
14. Deb, I.; Yoshikai, N. Org. Lett. 2013, 15, 4254-4257
15. Liang, Z.; Ju, L.; Xie, Y.; Huang, L.; Zhang, Y. Chem.-Eur. J. 2012, 18, 15816-15821
16. Blanchot, M.; Candito, D. A.; Larnand, F.; Lautens, M. Org. Lett. 2011, 13, 1486-1489
17. Peng, J.; Chen, T.; Chen, C.; Li, B. J. Org. Chem. 2011, 76, 9507-9513
18. Zhang, L.; Ang, G. Y.; Chiba, S. Org. Lett. 2010, 12, 3682-3685
19. Guo, W.; Li, S.; Tang, L.; Li, M.; Wen, L.; Chen, C. Org. Lett. 2015, 17, 1232-1235
20. Zhang, B.; Studer, A. Org. Lett. 2014, 16, 3990-3993
21. Deb, I.; Yoshikai, N. Org. Lett. 2013, 15, 4254-4257
22. Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323-5327
23. Yan, R.; Liu, X.; Pan, C.; Zhou, X.; Li, X.; Kang, X.; Huang, G. Org. Lett. 2013, 15, 4876-4879
24. Ji, X.; Huang, H.; Li, Y.; Chen, H.; Jiang, H. Angew. Chem., Int. Ed. 2012, 51, 7292-7296
25. Zhang, X.; Song, X.; Li, H.; Zhang, S.; Chen, X.; Yu, X.; Wang, W. Angew. Chem., Int. Ed. 2012, 51, 7282-7286
26. Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084-3213
27. Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50, 6164-6167
28. Jiang, H.; Cheng, Y.; Wang, R.; Zheng, M.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2013, 52, 13289-13292
29. Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792-10795
30. Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363-11366
31. Leifert, D.; Daniliuc, C. G.; Studer, A. Org. Lett. 2013, 15, 6286-6289
32. Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250-253
33. Jia, X.; Peng, F.; Qing, C.; Huo, C.; Wang, X. Org. Lett. 2012, 14, 4030-4033
34. Mitamura, T.; Iwata, K.; Ogawa, A. Org. Lett. 2009, 11, 3422-3424
35. Wang, Y.; Peng, F.; Liu, J.; Huo, C.; Wang, X.; Jia, X. J. Org. Chem. 2015, 80, 609-614
36. Jiang, H.; An, X.; Tong, K.; Zheng, T.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2015, 54, 4055-4059
37. Walton, J. C. Acc. Chem. Res. 2014, 47, 1406-1416
38. Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 4505-4519
39. McBurney, R. T.; Walton, J. C. J. Am. Chem. Soc. 2013, 135, 7349-7354
40. Markey, S. J.; Lewis, W.; Moody, C. J. Org. Lett. 2013, 15, 6306-6308
41. Mcburney, R. T.; Slawin, A. M. Z.; Smart, L. A.; Yu, Y.; Walton, J. C. Chem. Commun. 2011, 47, 7974-7976
42. Portela-Cubillo, F.; Scanlan, E. M.; Scott, J. S.; Walton, J. C. Chem. Commun. 2008, 4189-4191
43. Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. J. Org. Chem. 2008, 73, 5558-5565
44. Portela-Cubillo, F.; Surgenor, B. A.; Aitken, R. A.; Walton, J. C. J. Org. Chem. 2008, 73, 8124-8127
45. Alonso, R.; Campos, P. J.; Rodríguez, M. A.; Sampedro, D. J. Org. Chem. 2008, 73, 2234-2239
46. Alonso, R.; Campos, P. J.; García, B.; Rodríguez, M. A. Org. Lett. 2006, 8, 3521-3523
47. Gerfaud, T.; Neuville, L.; Zhu, J. Angew. Chem. Int. Ed. 2009, 48, 572-577
48. Huang, H.; Ji, X.; Tang, X.; Zhang, M.; Li, X.; Jiang, H. Org. Lett. 2013, 15, 6254-6257
49. Tang, X.; Huang, L.; Qi, C.; Wu, W.; Jiang, H. Chem. Commun. 2013, 49, 9597-9599
50. Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 4205-4208
51. Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, 1155-1171
52. Zhao, M.-N.; Hui, R.-R.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2014, 16, 3082-3085
53. Du, W.; Zhao, M.-N.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Chem. Commun. 2014, 50, 7437-7439
54. Ran, L.-F.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Green Chem. 2014, 16, 112-115
55. Coskun, N. Tetrahedron 1999, 55, 475-484
56. Carpino, L. A.; Giza, C. A.; Carpino, B. A. J. Am. Chem. Soc. 1959, 81, 955-957
57. King, F. D.; Walton, D. R. M. Synthesis 1975, 788-789
58. Ketz, E. U.; Zinner, G. Arch. Pharm. 1978, 311, 530-541
59. Leffler, J. E.; Bothner-By, A. A. J. Am. Chem. Soc. 1951, 73, 5473-5475
60. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
61. Xuan, J.; Lu, L. Q.; Chen, J. R.; Xiao, W.-J. Eur. J. Org. Chem. 2013, 2071-2075
62. Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387-2403
63. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687-7697
64. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828-6838
65. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
66. Yoon, T. P.; Ischay, M. A.; Du, J. Nature Chem. 2010, 2, 527-532
67. Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785-9789
68. Ali, A. A.; El Sayed, H. M.; Abdallah, O. M.; Steglich, W. Phytochemistry 1986, 25, 2399-2401
69. Giordani, R. B.; de Andrade, J. P.; Verli, H.; Dutilh, J. H.; Henriques, A. T.; Berkov, S.; Bastida, J.; Zuanazzi, J. A. S. Magn. Reson. Chem. 2011, 49, 668-672
70. Harayama, T.; Akamatsu, H.; Okamura, K.; Miyagoe, T.; Akiyama, T.; Abe, H.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 2001, 523-528
71. Portela-Cubillo, F.; Lymer, J.; Scanlan, E. M.; Scott, J. S.; Walton, J. C. Tetrahedron 2008, 64, 11908-11916
72. Banwell, M. G.; Lupton, D. W.; Ma, X.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741-2744
73. De, S.; Mishra, S.; Kakde, B. N.; Dey, D.; Bisai, A. J. Org. Chem. 2013, 78, 7823-7844 See also refs 3f,4f,7e-7g
74. Istvan, Z.; Rethy, B.; Hohmann, J.; Molnar, J.; Imre, O.; Falkay, G. In Vivo 2009, 23, 41-48
75. Caballero, A.; Campos, P. J.; Rodríguez, M. A. Tetrahedron 2013, 69, 4631-4635
76. Szlávik, L.; Gyuris, A.; Minárovits, J.; Forgo, P.; Molnár, J.; Hohmann, J. Planta Med. 2004, 70, 871-873