Synthesis of pyrrolo[3,4-c]quinolines by 1,5-electrocyclisation of non-stabilised azomethine ylides

Tetrahedron

Volumn 61, Issue 34, 2005, Pages 8199-8205

  Nyerges, Miklós ^a   Pintér, Áron ^a   Virányi, Andrea ^a   Blaskó, Gábor ^b   Toke, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b EGIS PHARMACEUTICALS LTD   (Hungary)

Author keywords

Azomethine ylide; Cycloaddition; Electrocyclisation; Pyrroles

Indexed keywords

AZOMETHINE YLIDE; MALEIMIDE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCYCLISATION; PRIORITY JOURNAL;

EID: 22544481128     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.032     Document Type: Article

References (38)

1. J.P. Michael Nat. Prod. Rep. 2004 650
2. J.P. Michael Nat. Prod. Rep. 2003 476
3. A.A. Alhaider, M.A. Abdelkader, and E.J. Lien J. Med. Chem. 28 1985 1398
4. S.F. Campbell, J.D. Hardstone, and M.J. Palmer J. Med. Chem. 31 1988 1031
5. D. Wu Tetrahedron 59 2003 8649
6. O. Meth-Cohn Heterocycles 35 1993 539
7. J.H. Rigby, and D.M. Danca Tetrahedron Lett. 38 1997 4969
8. S. Leue, W. Miao, A. Kanazawa, Y. Génisson, S. Garçon, and A.E. Greene J. Chem. Soc., Perkin Trans. 1 2001 2903
9. D.L. Comins, and J.M. Nolan Org Lett. 3 2001 1611
10. M. Toyota, C. Komori, and M. Ihara Heterocycles 56 2002 101
11. S.P. Chavan, and R. Sivappa Tetrahedron Lett. 45 2004 3113
12. S.P. Chavan, and R. Sivappa Tetrahedron 60 2004 9931
13. T. Harayama, Y. Morikami, Y. Shigeta, H. Abe, and Y. Takeuchi Synlett 2003 847
14. Z. Ma, and D.Y.Z. Lee Tetrahedron Lett. 45 2004 6721
15. L. Carles, K. Narkunan, S. Penlou, L. Rousset, D. Bouchu, and M.A. Ciufolini J. Org. Chem. 67 2002 4304
16. This work has been published in preliminary form: A. Pintér, M. Nyerges, A. Virányi, and L. Tõke Tetrahedron Lett. 44 2003 2343
17. For excellent reviews on 1,5-dipolar cyclisations, see: (a) E.C. Taylor, and I.J. Turchi Chem. Rev. 79 1979 181
18. R. Huisgen Angew. Chem., Int. Ed. Engl. 19 1980 947
19. There have been only a few reports on the preparation pyrrolo[3,4-c]quinolines: (a) L. Horner Justus Liebigs Ann. Chem. 548 1941 117
20. R.B. Roy, and G.A. Swan J. Chem. Commun. 1968 1446
21. R.B. Roy, and G.A. Swan J. Chem. Soc. C 1969 1886
22. G. Murata, H. Satoru, K. Teramato, M. Miura, and M. Nomura Heterocycles 36 1993 2147
23. G.A. Swan, R.B. Roy, and G.D. Khandelwal J. Chem. Soc. 1974 891
24. K. Jones, and J. Wilkinson J. Chem. Soc., Chem. Commun. 1992 1767
25. S.J. Veenstra, R. Fortgens, R.J. Vijn, B.S. Jong, and W.N. Speckamp Tetrahedron 43 1987 1147
26. W.-F. Gündel, and S.Z. Bohnert Naturforschung 40b 1985 1409
27. A. Virányi, M. Nyerges, G. Blaskó, and L. Toke Synthesis 2003 2655
28. O. Meth-Cohn, and B. Narine Tetrahedron Lett. 19 1978 2045
29. O. Meth-Cohn, B. Narine, and B. Tarnowski J. Chem. Soc., Perkin Trans. 1 1981 1520
30. O. Tsuge, S. Kanemasa, M. Ohe, and S. Takenaka Bull. Chem. Soc. Jpn. 60 1987 4079
31. M. Nyerges, L. Balázs, I. Bitter, I. Kádas, I. Kövesdi, and L. Toke Tetrahedron 51 1995 6783
32. A. Arany, P.W. Groundwater, and M. Nyerges Tetrahedron Lett. 39 1998 3267
33. O. Tsuge, and S. Kanemasa Adv. Heterocycl. Chem. 45 1989 232 349
34. M. Nyerges, A. Arany, I. Fejes, P.W. Groundwater, W. Zhang, D. Bendell, R.J. Anderson, and L. Toke Tetrahedron 58 2002 989
35. P.W. Groundwater, and M. Nyerges Adv. Heterocycl. Chem. 73 1999 97 129
36. A. Arany, D. Bendell, P.W. Groundwater, I. Garnett, and M. Nyerges J. Chem. Soc., Perkin Trans. 1 1999 2605
37. M. Nyerges, A. Virányi, Á. Pintér, and L. Tõke Tetrahedron Lett. 44 2003 793
38. Á. Pintér, M. Nyerges, A. Virányi, I. Bitter, and L. Toke Tetrahedron Lett. 46 2005 377