Palladium-catalysed synthesis of dibenzo[de,g]quinolines. A novel approach to the B-ring system of aporphine-related heterocycles

European Journal of Organic Chemistry

Volumn , Issue 8, 1999, Pages 1957-1961

  Gies, Anne Elisabeth ^a   Pfeffer, Michel ^a   Sirlin, Claude ^a   Spencer, John ^a,b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b THROMBOSIS RESEARCH INSTITUTE   (United Kingdom)

Author keywords

Aporphines; Dibenzo de,g quinolines; Homogeneous catalysis; Nitrogen heterocycles; Palladium

Indexed keywords

APORPHINE DERIVATIVE; BOLDINE; DIBENZO[DE,G]QUINOLINE DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; PALLADIUM; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032768846     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199908)1999:8<1957::aid-ejoc1957>3.0.co;2-i     Document Type: Article

References (24)

1. A. D. Ryabov, Chem. Rev. 1990, 90, 403-424.
2. [2a] M. Pfeffer, Recl. Trav. Chem. Pays-Bas 1990, 109, 567-576.
3. [2b] M. Pfeffer, Pure & Applied Chem. 1992, 64, 335-342.
4. [2c] J. Spencer, M. Pfeffer in: Advances in Metal-Organic Chemistry (Ed.: L. S. Liebeskind), JAI Press, London, 1998, vol. 6, 103-144.
5. [3a] R. C. Larock, E. K. Yum, J. Am. Chem. Soc. 1991, 113, 6689-6690.
6. [3b] K. R. Roesch, R. C. Larock, J. Org. Chem. 1998, 63, 5306-5307.
7. [3c] R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem. 1998, 63, 7652-7662 and refs. cited therein.
8. M. Pfeffer, N. Beydoun, Synthesis 1990, 729-732.
9. [5a] R. Hansel, Phytopharmaka, 2nd edn., Springer-Verlag, Berlin, 1991, p.186-191.
10. [5b] G. L. Gessa, G. U. Corsini in: Apomorphine and Other Dopaminomimetics, Raven Press, New York, 1981, Vol. 1 Basic Pharmacology, Vol. 2 Clinical Pharmacology.
11. [5c] K. Likhitwitaywuid, C. K. Angerhofer, H. Y. Chai, J. M. Pezzuto, G. A. Cordell, N. Ruangrungsi, Lloydia 1993, 56, 1468-1478.
12. [6a] F. Roblot, R. Hocquemiller, A. Cavé, Bull. Soc. Chim. Fr. 1990, 127, 258-267.
13. [6b] Y. Landais, J. P. Robin, Tetrahedron 1992, 48, 7185-7196.
14. [6c] I. W. Southon, J. Buckingham, Dictionary of Alkaloids, Chapman and Hall, New-York, 1989.
15. [7a] M. A. Goldberg, E. P. Ordas, G. Carsh, J. Am. Chem. Soc. 1947, 69, 260-262.
16. [7b] L. F. Fieser, R. P. Jacobsen, C. C. Price, J. Am. Chem. Soc. 1936, 58, 2163-2166.
17. K. Nishiyama, N. Tanaka, J. Chem. Soc. Chem. Commun. 1983, 1322-1323.
18. M. Pfeffer, N. Sutter-Beydoun, A. de Cian, J. Fischer, J. Organomet. Chem. 1993, 453, 139-146.
19. Under the same conditions, however, 3c only afforded a 1:1 mixture of both starting material and product 6a after 48 h in refluxing N-methylpyrrolidine.
20. [11a] J. Spencer, M. Pfeffer, A. DeCian, J. Fischer, J. Org. Chem. 1995, 60, 1005-1012.
21. [11b] M. Pfeffer, M. A. Rotteveel, G. Le Borgne, J. Fischer, J. Org. Chem. 1992, 57, 2147-2154.
22. [11c] J. Spencer, M. Pfeffer, N. Kyritsakas, J. Fischer, Organometallics, 1995, 14, 2214-2224.
23. A.-E. Gies, M. Pfeffer, J. Org. Chem. 1999.
24. H. M. Colqhoun, J. Holton, D. J. Thompson, M. V. Twigg in New Pathways for Organic Synthesis: Practical Applications of Transition Metals, Plenum Press, New York & London, 1984.