Efficient synthesis of aza-heterocycles by a domino process using an inter- and an intramolecular Heck reaction

Synlett

Volumn , Issue 2, 1998, Pages 145-146

  Tietze, Lutz F ^a   Ferraccioli, Raffaella ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002451986     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1602     Document Type: Article

References (29)

1. (a) Heck, R. F. Org. React. 1982, 27, 345.
2. (b) Heck, R.F. Palladium Reagents in Organic Synthesis, Academic Press, London 1985.
3. (c) Daves, G. D.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
4. (d) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473;
5. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
6. (e) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
7. (f) Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
8. (g) Shibasaki, M.; Boden, D. J.; Kojima, A. Tetrahedron, 1997, 53, 7371.
9. (a) Schimpf, R.; Tietze, L.F. Angew. Chem. 1994, 106, 1138;
10. Angew. Chem. Int. Ed. Engl. 1994, 33, 1089.
11. (b) Tietze, L. F.; Raschke, T. Synlett, 1995, 597.
12. (a) Tietze, L. F.; Nöbel, T.; Spescha, M. Angew. Chem. 1996, 108, 2385;
13. Angew. Chem. Int. Ed. Engl. 1996, 35, 2259.
14. (b) Tietze, L. F.; Schirok, H. Angew. Chem. 1997, 109, 1159;
15. Angew. Chem. Int. Ed. Engl. 1997, 36, 1124.
16. Boger, D. L.; Johnson, D. S. Angew. Chem. 1996, 108, 1542;
17. Angew. Chem. Int. Ed. Engl. 1996, 35, 1438.
18. (a) Tufariello, J.J.; Meckler, H; Senaratne, K. P. A. Tetrahedron, 1985, 41, 3447.
19. (b) Wiseman, J. R.; Lee, S.Y. J. Org. Chem. 1986, 51, 2485.
20. (c) Vernon, P.; Gallagher, T. J. Chem. Soc., Chem. Commun., 1987, 245.
21. Kraus, G. A., Neuenschwander, K., J. Org. Chem. 1981, 46, 4791.
22. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667.
23. 2O (60/40), UV monitor (220 nm)
24. 2 calcd. 307.0207, found 307.0208.
25. 2O (1/1/0.2) as solvent (29%).
26. 2: calcd. C 73.99, H 5.77, N 6.16; found C 73.85, H 5.59, N 6.25.
27. Herrmann, A. W.; Brossmer, C.; Öfele, K.; Reisiger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989;
28. Angew. Chem., Int. Ed., Engl., 1995, 34, 1844
29. 3 is not suitable as a solvent since decomposition of 4 and 8 occurs. At room temperature 4, 5, 7, 8 show a double set of signals.