Facile synthesis of substituted isoquinolines

Tetrahedron Letters

Volumn 53, Issue 16, 2012, Pages 2125-2128

  Chang, Meng Yang ^a   Wu, Ming Hao ^a   Lee, Nein Chia ^a   Lee, Ming Fang ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Claisen rearrangement; Isoquinoline; One pot combination reaction; Papaverine

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; AMMONIUM ACETATE; BENZALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; ISOQUINOLINE DERIVATIVE; OSMIUM DERIVATIVE; PAPAVERINE; SODIUM IODATE;

ADDITION REACTION; ARTICLE; CLAISEN REARRANGEMENT; GRIGNARD REACTION; METHYLATION; ONE POT SYNTHESIS; OXIDATION; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84862804466     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.045     Document Type: Article

References (29)

1. For reviews on the synthesis of isoquinolines, see: M. Chrzanowska, and M.D. Rozwadowska Chem. Rev. 104 2004 3341
2. E.L. Larghi, M.L. Bohn, and T.S. Kaufman Tetrahedron 65 2009 4257
3. M.D. Rozwadowska Heterocycles 39 1994 903
4. S. Brase, C. Gil, and K. Knepper Bioorg. Med. Chem. 10 2002 2415
5. A.N. Flyer, C. Si, and A.G. Myers Nat. Chem. 2 2010 886
6. N. Guimond, and K. Fagnou J. Am. Chem. Soc. 131 2009 12050
7. F. Sha, and X. Huang Angew. Chem., Int. Ed. 48 2009 3458
8. Y. Watanabe, S. Aoki, D. Tanabe, A. Setiawan, and M. Kobayashi Tetrahedron 63 2007 4074
9. X. Wei, M. Zhao, Z. Du, and X. Li Org. Lett. 13 2011 4636
10. N. Todorovic, E. Awuah, S. Albu, C. Ozimok, and A. Capretta Org. Lett. 13 2011 6180 and cited references therein
11. For nigellimine (1), see: Atta-ur-Rahman, S. Malik, and K. Zaman J. Nat. Prod. 55 1992 676
12. For papaverine (2), see: J.R. Falck, S. Manna, and C. Mioskowski J. Org. Chem. 46 1981 3742
13. For necatorone (3), see: J.-D. Klamann, B. Fugmann, and W.P. Steglich Phytochemistry 28 1989 3519
14. For refescine (4), see: M.D. Menachery, C.D. Muthler, and K.T. Buck J. Nat. Prod. 50 1987 726
15. For decumbenine B (5), see: J. Zhang, D. Zhu, and S. Hong Phytochemistry 39 1995 435
16. For berberine (6), see: Y.-X. Wang, Y.-P. Wang, H. Zhang, W.-J. Kong, Y.-H. Li, F. Liu, R.-M. Gao, T. Liu, J.-D. Jiang, and D.-Q. Song Bioorg. Med. Chem. Lett. 19 2009 6004
17. W.J. Gensler R. Adams, Org. React Vol. 6 1951 Wiley New York 191 206
18. W.M. Whaley, and T.R. Govindachari R. Adams, Organic Reactions Vol. 6 1951 Wiley New York 74 150
19. W.M. Whaley, and T.R. Govindachari R. Adams, Organic Reactions Vol. 6 1951 Wiley New York 154 190
20. S.K. Chattopadhyay, T. Biswas, and S. Maity Synlett 2006 2211
21. J.-C. Tsai, S.-R. Li, L.-Y. Chen, P.Y. Chen, J.Y. Jhong, C.-J. Shu, Y.-F. Lo, C.-N. Lin, and E.-C. Wang J. Chin. Chem. Soc. 55 2008 1317
22. W. Yu, Y. Mei, Y. Kang, Z. Hua, and Z. Jin Org. Lett. 6 2004 3217
23. T.E. Nielsen, and M. Meldal Org. Lett. 7 2005 2695
24. T.E. Nielsen, S.T. Le Quement, and M. Meldal Org. Lett. 9 2007 2469
25. X. Huang, K.S.E. Tanaka, and A.J. Bennet J. Am. Chem. Soc. 119 1997 11147
26. P. Schiess, M. Huys-Francotte, and C. Vogel Tetrahedron Lett. 26 1985 3959
27. L. Pongo, B. Agai, F. Faigl, J. Reiter, and G. Simig J. Heterocycl. Chem. 43 2006 1539
28. G. Bringmann Liebigs Ann. Chem. 1985 2126
29. Li, Y.-L.; Combs, A. P.; Yue, E. W.; Li, H.-Y. WO patent 2011075630.