Synthesis of 12-oxobenzo[c]phenanthridinones and 4-substituted 3-arylisoquinolones via Vilsmeier-Haack reaction

Tetrahedron

Volumn 68, Issue 1, 2012, Pages 250-261

  Khadka, Daulat Bikram ^a   Yang, Su Hui ^a   Cho, Suk Hee ^a   Zhao, Chao ^a   Cho, Won Jea ^a  

^a Chonnam National University   (South Korea)

Author keywords

12 Oxobenzo c phenanthridinone; 4 Substituted 3 arylisoquinolone; Knoevenagel condensation; Mitsunobu reaction; Vilsmeier Haack reaction

Indexed keywords

12 OXOBENZO[C]PHENANTHRIDINONE; 3 ARYL 4 PHENOXYMETHYLISOQUINOLONE; 3 ISOQUINOLINYL 2 PHENYL ACRYLONITRILE; 4 ALKOXYMETHYL 3 ARYLISOQUINOLONE; 4 AMINOMETHYL 3 ARYLISQUINOLONE; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; VILSMEIER HAACK REACTION;

EID: 82255175372     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.053     Document Type: Article

References (30)

1. V.A. Glushkov, and Y.V. Shklyaev Chem. Heterocycl. Compd. 37 2001 663
2. G.R. Pettit, Y. Meng, D.L. Herald, K.A. Graham, R.K. Pettit, and D.L. Doubek J. Nat. Prod. 66 2003 1065
3. M.C. González, M.C. Zafra-Polo, M.A. Blázquez, A. Serrano, and D. Cortes J. Nat. Prod. 60 1997 108
4. A. Patra, C.T. Montgomery, A.J. Freyer, H. Guinaudeau, M. Shamma, B. Tantisewie, and K. Pharadai Phytochemistry 26 1987 547
5. H. Ishii, T. Ishikawa, M. Akaike, T. Tohjoh, M. Toyoki, M. Ishikawa, I.S. Chen, and S.T. Lu Yakugaku Zasshi 104 1984 1030
6. W.J. Cho, S.Y. Min, T.N. Le, and T.S. Kim Bioorg. Med. Chem. Lett. 13 2003 4451
7. T. Matsui, T. Sugiura, H. Nakai, S. Iguchi, S. Shigeoka, H. Takada, Y. Odagaki, Y. Nagao, Y. Ushio, K. Ohmoto, H. Iwamura, S. Yamazaki, Y. Arai, and M. Kawamura J. Med. Chem. 35 1992 3307
8. W.J. Cho, S.J. Yoo, B.H. Chung, B.G. Choi, S.H. Cheon, S.H. Whang, S.K. Kim, B.H. Kang, and C.O. Lee Arch. Pharm. Res. 19 1996 321
9. M. Fosset, J.R. De Weille, R.D. Green, H. Schmid-Antomarchi, and M. Lazdunski J. Biol. Chem. 263 1988 7933
10. C.Y. Watson, W.J. Whish, and M.D. Threadgill Bioorg. Med. Chem. 6 1998 721
11. P. Ray, J. Wright, J. Adam, S. Boucharens, D. Black, A.R. Brown, O. Epemolu, D. Fletcher, M. Huggett, P. Jones, S. Laats, A. Lyons, J. de Man, R. Morphy, B. Sherborne, L. Sherry, N. Straten, P. Westwood, and M. York Bioorg. Med. Chem. Lett. 21 2011 1084
12. S.W. Li, M.G. Nair, D.M. Edwards, R.L. Kisliuk, Y. Gaumont, I.K. Dev, D.S. Duch, J. Humphreys, G.K. Smith, and R. Ferone J. Med. Chem. 34 1991 2746
13. Q. Chao, L. Deng, H. Shih, L.M. Leoni, D. Genini, D.A. Carson, and H.B. Cottam J. Med. Chem. 42 1999 3860
14. M. Kimura, I. Waki, Y. Deguchi, K. Amemiya, and T. Maeda Chem. Pharm. Bull. 31 1983 1277
15. M.C. Johnson, Q. Hu, L. Lingardo, R.A. Ferre, S. Greasley, J. Yan, J. Kath, P. Chen, J. Ermolieff, and G. Alton J. Comput. Aided Mol. Des. 25 2011 689
16. H.T. Van, S.H. Yang, D.B. Khadka, Y.C. Kim, and W.J. Cho Tetrahedron 65 2009 10142
17. T.N. Le, and W.J. Cho Chem. Pharm. Bull. 56 2008 1026
18. T.N. Le, and W.J. Cho Bull. Korean Chem. Soc. 28 2007 763
19. T.N. Le, and W.J. Cho Chem. Pharm. Bull. 54 2006 476
20. T.N. Le, and W.J. Cho Chem. Pharm. Bull. 53 2005 118
21. D.B. Khadka, and W.J. Cho Bioorg. Med. Chem. 19 2011 724
22. E. Kiselev, T.S. Dexheimer, Y. Pommier, and M. Cushman J. Med. Chem. 53 2010 8716
23. J.C. Wang Annu. Rev. Biochem. 65 1996 635
24. J.J. Champoux Annu. Rev. Biochem. 70 2001 369
25. J.C. Wang Nat. Rev. Mol. Cell Biol. 3 2002 430
26. M. Iwata, and S. Emoto Bull. Chem. Soc. Jpn. 47 1974 1687
27. M.S. Pedras, and M. Jha J. Org. Chem. 70 2005 1828
28. I.M. Downie, M.J. Earle, H. Heaney, and K.F. Shuhaibar Tetrahedron 49 1993 4015
29. W.J. Cho, S.J. Yoo, M.J. Park, B.H. Chung, and C.O. Lee Arch. Pharm. Res. 20 1997 264
30. G.S. Poindexter J. Org. Chem. 47 1982 3787