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

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2343-2346

  Pintér, Áron ^a   Nyerges, Miklós ^a   Virányi, Andrea ^a   Toke, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; MALEIMIDE DERIVATIVE; QUINOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; CYCLIZATION; DIPOLE; ELECTROCYCLIZATION; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037430427     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00232-6     Document Type: Article

References (27)

1. Meth-Cohn O. Heterocycles. 35:1993;539.
2. Rigby J.H., Danca D.M. Tetrahedron Lett. 38:1997;4969.
3. Leue S., Miao W., Kanazawa A., Génisson Y., Garçon S., Greene A.E. J. Chem. Soc., Perkin Trans. 1. 2001;2903.
4. Comins D.L., Nolan J.M. Org. Lett. 2001;1611.
5. Toyota M., Komori C., Ihara M. Heterocycles. 56:2002;101.
6. Carles L., Narkunan K., Penlou S., Rousset L., Bouchu D., Ciufolini M.A. J. Org. Chem. 67:2002;4304.
7. For excellent reviews on 1,5-dipolar cyclisations, see: (a) Taylor, E. C.; Turchi, I. J. Chem. Rev. 1979, 79, 181;
8. (b) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 947.
9. There have been only a few reports on the preparation of pyrrolo[3,4-c]quinolines and none of them generally applicable to the synthesis of these heterocycles: (a) Horner, L. Justus Liebigs Ann. Chem. 1941, 548, 117;
10. (b) Roy, R. B.; Swan, G. A. J. Chem. Commun. 1968, 1446;
11. (c) Roy, R. B.; Swan, G. A. J. Chem. Soc. C 1969, 1886;
12. (d) Murata, G.; Satoru, H.; Teramato, K.; Miura, M.; Nomura, M. Heterocycles 1993, 36, 2147;
13. (e) Swan, G. A.; Roy, R. B.; Khandelwal, G. D. J. Chem. Soc. 1974, 891;
14. (f) Jones, K.; Wilkinson, J. J. Chem. Soc., Chem. Commun. 1992, 1767-1769;
15. (g) Veenstra, S. J.; Fortgens, R.; Vijn, R. J.; Jong, B. S.; Speckamp, W. N. Tetrahedron 1987, 43, 1147-1156;
16. (h) Gündel, W.-F.; Bohnert, S. Z. Naturforsch. 1985, 40b, 1409.
17. Meth-Cohn O., Narine B. Tetrahedron Lett. 19:1978;2045.
18. Meth-Cohn O., Narine B., Tarnowski B. J. Chem. Soc., Perkin Trans. 1. 1981;1520.
19. Tsuge O., Kanemasa S., Ohe M., Takenaka S. Bull. Chem. Soc. Jpn. 60:1987;4079.
20. Nyerges M., Balázs L., Bitter I., Kádas I., Kövesdi I., Toke L. Tetrahedron. 51:1995;6783.
21. Arany A., Groundwater P.W., Nyerges M. Tetrahedron Lett. 39:1998;3267.
22. 3).
23. 3).
24. Tsuge O., Kanemasa S. Adv. Heterocycl. Chem. 45:1989;232-349.
25. Nyerges M., Arany A., Fejes I., Groundwater P.W., Zhang W., Bendell D., Anderson R.J., Toke L. Tetrahedron. 58:2002;989.
26. Groundwater P.W., Nyerges M. Adv. Heterocycl. Chem. 73:1999;97-129.
27. Arany A., Bendell D., Groundwater P.W., Garnett I., Nyerges M. J. Chem. Soc., Perkin Trans. 1. 1999;2605.