Copper(I)-catalyzed intramolecular addition of N-chloroamides to double bonds; an efficient synthesis of lactams from unsaturated amides

Synthesis

Volumn , Issue 12, 2003, Pages 1886-1890

  Schulte Wülwer, Iris Anne ^a   Helaja, Juho ^a   Göttlich, Richard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Catalysis; Copper; Lactams; Radical reactions

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; SALTS; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR ADDITION;

NITROGEN COMPOUNDS;

AMIDE; CARBON; COPPER; COPPER DERIVATIVE; LACTAM; N CHLOROAMIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0141742415     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40997     Document Type: Article

References (17)

1. (a) Dalton, D. R. The Alkaloids; Marcel Dekker: New York, 1979.
2. (b) Gilchrist, T. L. Heterocyclenchemie; VCH: Weinheim, 1995.
3. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
4. (a) Kuehne, M. E.; Horne, D. A. J. Org. Chem. 1975, 40, 1278.
5. (b) Lessard, J.; Cote, R.; Mackiewicz, P.; Furstoss, R.; Waegell, B. J. Org. Chem. 1978, 43, 3750.
6. (a) Göttlich, R. Synthesis 2000, 1561.
7. (b) Heuger, G.; Kalsow, S.; Göttlich, R. Eur. J. Org. Chem. 2002, 1848.
8. (a) Kochi, J. K. Free Radicals; Wiley: New York, 1973.
9. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
10. Bowden, K.; Heilbron, I.; Jones, E.; Weedon, B. J. Chem. Soc. 1946, 39.
11. 2O with toluene and then recrystallised from toluene.
12. Compounds 5b-f are known, see (4) and: (a) Toshimitsu, A.; Terao, K.; Uemura, S. J. Org. Chem. 1986, 51, 1724. (b) Sennyey, G.; Barcelo, G.; Senet, J.-P. Tetrahedron Lett. 1987, 28, 5809.
13. Compounds 5b-f are known, see (4) and: (a) Toshimitsu, A.; Terao, K.; Uemura, S. J. Org. Chem. 1986, 51, 1724. (b) Sennyey, G.; Barcelo, G.; Senet, J.-P. Tetrahedron Lett. 1987, 28, 5809.
14. Blenderman, W. G.; Joullie, M. M.; Preti, G. J. Org. Chem. 1983, 48, 3206.
15. Hanko, R.; Hoppe, D. Angew. Chem. 1981, 93, 115.
16. (a) Newcomb, M.; Esker, J. L. Tetrahedron Lett. 1991, 32, 1035.
17. (b) Clark, A. J.; Peacock, J. L. Tetrahedron Lett. 1998, 39, 6029.