Synthesis of 6-carboxylated phenanthridines by oxidative alkoxycarbonylation-cyclization of 2-isocyanobiphenyls with carbazates

Tetrahedron Letters

Volumn 55, Issue 38, 2014, Pages 5338-5341

  Wang, Gao ^a   Chen, Shan Yong ^a   Yu, Xiao Qi ^a  

^a Sichuan University   (China)

Author keywords

Alkoxycarbonylation cyclization; Carbazates; Phenanthridines

Indexed keywords

BIPHENYL DERIVATIVE; PHENANTHRIDINE DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYST; CYCLIZATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; OXIDATION; REACTION TIME;

EID: 84906957866     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.07.049     Document Type: Article

References (36)

1. S.D. Phillips, and R.N. Castle J. Heterocycl. Chem. 18 1981 223
2. M. Suffness, and G.A. Cordell The Alkaloids 1985 Academic Press New York Vol. 25, p 178
3. S. Simeon, J.L. Rios, and A. Villar Pharmazie 44 1989 593
4. T. Nakanishi, and M. Suzuki Org. Lett. 1 1999 985
5. O.B. Abdel-Halim, T. Morikawa, S. Ando, H. Matsuda, and M. Yoshikawa J. Nat. Prod. 67 2004 1119
6. L. Sripada, J.A. Teske, and A. Deiters Org. Biomol. Chem. 6 2008 263
7. R.B. Giordani, J.P. de Andrade, H. Verli, J.H. Dutilh, A.T. Henriques, S. Berkov, J. Bastid, and J.A.S. Zuanazzia Magn. Reson. Chem. 49 2011 668
8. S. Fang, L. Wang, and S.M. Hecht J. Org. Chem. 58 1993 5025
9. I.L. Tsai, M.F. Wun, C.M. Teng, T. Ishikawa, and I.S. Chen Phytochemistry 48 1998 1377
10. T. Ishikawa Med. Res. Rev. 21 2001 61
11. W.A. Denny Curr. Med. Chem. 9 2002 1655
12. O.B. Abdel-Halim, T. Morikawa, S. Ando, H. Matsuda, and M. Yoshikawa J. Nat. Prod. 67 2004 7
13. P.H. Bernardo, K.F. Wan, T. Sivaraman, J. Xu, F.K. Moore, A.W. Hung, H.Y.K. Mok, V.C. Yu, and C.L.L. Chai J. Med. Chem. 51 2008 6699
14. E. Dubost, N. Dumas, C. Fossey, R. Magnelli, S. Butt-Gueulle, C. Balladonne, D.H. Caignard, F. Dulin, J.S. d.-O.Santos, P. Millet, Y. Charnay, S. Rault, T. Cailly, and F. Fabis J. Med. Chem. 55 2012 9693
15. S.L. Bondarev, V.N. Knyukshto, S.A. Tikhomirov, and A.N. Pyrko Opt. Spectrosc. 100 2006 386
16. N. Stevens, N. O'Connor, H. Vishwasrao, D. Samaroo, E.R. Kandel, D.L. Akins, C.M. Drain, and N.J. Turro J. Am. Chem. Soc. 130 2008 7182
17. I. Ryu, N. Sonoda, and D.P. Curran Chem. Rev. 96 1996 177
18. G.Y.S. Qiu, Q.P. Ding, and J. Wu Chem. Soc. Rev. 42 2013 5257
19. B. Zhang, C. Mck-Lichtenfeld, C.G. Daniliuc, and A. Studer Angew. Chem., Int. Ed. 52 2013 10792
20. Q.L. Wang, X.C. Dong, T.B. Xiao, and L. Zhou Org. Lett. 15 2013 4846
21. Y.Z. Cheng, H. Jiang, Y. Zhang, and S. Yu Org. Lett. 15 2013 5520
22. D. Leifert, C.G. Daniliuc, and A. Studer Org. Lett. 15 2013 6286
23. J. Liu, C. Fan, H. Yin, C. Qin, G. Zhang, X. Zhang, H. Yi, and A. Lei Chem. Commun. 2014 2145
24. M. Tobisu, K. Koh, T. Furukawa, and N. Chatani Angew. Chem., Int. Ed. 51 2012 11363
25. H. Jiang, Y. Cheng, R. Wang, M. Zheng, Y. Zhang, and S. Yu Angew. Chem., Int. Ed. 52 2013 13289
26. B. Zhang, C.G. Daniliuc, and A. Studer Org. Lett. 16 2014 250
27. I. Ryu, and N. Sonoda Angew. Chem., Int. Ed. 35 1996 1050
28. I. Ryu Chem. Soc. Rev. 30 2001 16
29. A. Brennführer, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 48 2009 4114
30. T. Taniguchi, Y. Sugiura, H. Zaimoku, and H. Ishibashi Angew. Chem., Int. Ed. 49 2010 10154
31. Y. Su, Z. Wu, and S. Tian Chem. Commun. 2013 6528
32. X. Xu, Y. Tang, X. Li, G. Hong, M. Fang, and X. Du J. Org. Chem. 79 2014 446
33. G. Wang, S. Wang, J. Wang, S. Chen, and X. Yu Tetrahedron 70 2014 3466
34. T. Xiao, L. Li, G. Lin, Q. Wang, P. Zhang, Z. Mao, and L. Zhou Green Chem. 16 2014 2418
35. During the preparation of this Letter, a similar tetrabutylammonium iodide-catalyzed reaction was reported (Li, X.; Fang, M.; Hu, P.; Hong, G.; Tang, Y.; Xu, X. Adv. Synth. Catal. 2014, 356, 2103). Using our conditions, by comparison, we might reduce the dosage of raw material and the reaction time. Meanwhile, higher yield was obtained.
36. C. Pan, J. Han, H. Zhang, and C. Zhu J. Org. Chem. 79 2014 5374