Heck reactions of quinoline-derived nonaflates

Synlett

Volumn , Issue 18, 2006, Pages 2993-2996

  Aulenta, Francesca ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Heck coupling; Nonaflate; Pd catalysis; Quinoline; Samarium(II) iodide

Indexed keywords

ALKENE; KETONE; QUINOLINE DERIVATIVE; QUINOLYL NONAFLATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33751291498     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948197     Document Type: Article

References (40)

1. (a) Berndt, M.; Hlobilová, I.; Reissig, H.-U. Org. Lett. 2004, 6, 957.
2. (b) Review: Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422.
3. For recent reviews on azasteroids see: (a) Senthilkumar, S. P. Curr. Org. Chem. 2004, 8, 1521.
4. (b) Burbiel, J.; Bracher, F. Steroids 2003, 68, 587.
5. For selected publications: (c) Oumzil, K.; Ibrahim-Ouali, M.; Santelli, M. Synlett 2005, 1695.
6. (d) Dolle, R. E.; Allaudeen, H. S.; Kruse, L. I. J. Med. Chem. 1990, 33, 877.
7. (e) Brandt, M.; Levy, M. A. Biochemistry 1989, 28, 140.
8. (f) Gandiha, A.; Marshall, G.; Paul, D.; Singh, H. J. Pharm. Pharmacol. 1974, 26, 871.
9. (a) Heck, R. F.; Nolley, J. P. Jr. J. Org. Chem. 1972, 37, 2320.
10. (b) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
11. Reviews: (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
12. (d) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379;
13. Angew. Chem. 1994, 106, 2473.
14. (e) For a scope of reaction conditions, see: Bräse, S.; de Meijere, A. Cross-Coupling of Organyl Halides with Alkenes: the Heck Reaction, In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 1998, 217.
15. For the synthesis of 7 see also: Martinez, A. G.; Fernandez, A. H.; Alvarez, R. M. M. Synthesis 1984, 481.
16. (a) Tundel, R. E.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2006, 71, 430.
17. (b) Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P. Org. Lett. 2005, 7, 4871.
18. (c) Flögel, O.; Dash, J.; Brüdgam, I.; Hartl, H.; Reissig, H.-U. Chem. Eur. J. 2004, 10, 4283.
19. (d) Dash, J.; Lechel, T.; Reissig, H.-U. unpublished results.
20. (e) Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771.
21. (f) Rottländer, M.; Knochel, P. J. Org. Chem. 1998, 63, 203.
22. (g) Roth, G. P.; Fuller, C. E. J. Org. Chem. 1991, 56, 3493.
23. Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293.
24. (a) Dyker, G.; Kadzimirsz, D. Eur. J. Org. Chem. 2003, 3167.
25. (b) Padwa, A.; Zanka, A.; Harris, J. M. Tetrahedron 2003, 59, 4939.
26. (c) Dyker, G.; Thöne, A. J. Prakt. Chem. 1999, 341, 138.
27. (d) Jeffery, T. Tetrahedron Lett. 1990, 31, 6641.
28. (a) Jeffery, T. Tetrahedron 1996, 52, 10113.
29. (b) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
30. (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
31. (b) Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron Lett. 1995, 36, 6287.
32. 3: 340.17868; found: 340.17944.
33. Formation of a stable dimeric complex would also be plausible.
34. Beletskaya, I. P.; Gamina, O. G.; Tsvetkov, A. V.; Fedorov, A. Y.; Finet, J.-P. Synlett 2004, 2797.
35. (a) Gross, S.; Reissig, H.-U. Org. Lett. 2003, 5, 4305.
36. (b) Gross, S.; Reissig, H.-U. Synlett 2002, 2027.
37. (c) Berndt, M.; Reissig, H.-U. Synlett 2001, 1290.
38. (d) Nandanan, E.; Dinesh, C. U.; Reissig, H.-U. Tetrahedron 2000, 56, 4277.
39. (e) Dinesh, C. U.; Reissig, H.-U. Angew. Chem. Int. Ed. 1999, 38, 789;
40. Angew. Chem. 1999, 111, 874.