Synthesis of 3-phenyl-4-piperidones from acetophenone by shapiro and azamichael reactions and their further derivatization

European Journal of Organic Chemistry

Volumn , Issue 26, 2007, Pages 4376-4382

  Rosiak, Anna ^a,c   Hoenke, Christoph ^b   Christoffers, Jens ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

^c EVONIK INDUSTRIES AG   (Germany)

Author keywords

Heterocycles; Hydrazones; Ketones; Piperidines; Protecting groups; Shapiro reaction

Indexed keywords

EID: 34548718807     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700325     Document Type: Article

References (51)

1. a) K. Hohenlohe-Oehringen, Monatsh. Chem. 1965, 96, 262-265;
2. b) H. Ott, R. Süess, German Patent, DE 2123328, 1971 [Chem. Abstr. 1972, 76, 72495];
3. c) H. Ott, R. Süess, German Patent, DE 2352909, 1974 [Chem. Abstr. 1974, 81, 25645];
4. d) D. Flockerzi, K. Klemm, H. Amschler, V. Figala, R. Beume, D. Häfner, G. Hanauer, M. Eltze, C. Schudt, U. Kilian, World Patent, WO 9117991 A1, 1991 [Chem. Abstr. 1992, 116, 151742];
5. e) R. Engelstätter, R. Beume, U. Kilian, C. Schudt, R. Riedel, H. Amschler, D. Flockerzi, German Patent, DE 4310050 A1, 1993; [Chem. Abstr. 1994, 120, 45952].
6. a) S. Cicchi, J. Revuelta, A. Zanobini, M. Betti, A. Brandi, Synlett 2003, 2305-2308;
7. b) R. Shintani, N. Tokunaga, H. Doi, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 6240-6241;
8. c) R. B. C. Jagt, J. G. de Vries, B. L. Feringa, A. J. Minnaard, Org. Lett. 2005, 7, 2433-2435;
9. d) R. Sebesta, M. G. Pizzuti, A. J. Boersma, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2005, 1711-1713;
10. e) C. Lin, H. Fang, Z. Tu, J.-T. Liu, C.-F Yao, J. Org. Chem. 2006, 71, 6588-6591;
11. f) B. Kranke, H. Kunz, Org. Biomol. Chem. 2007, 5, 349-354;
12. g) for a review, see: S. Laschat, T. Dickner, Synthesis 2000, 1781-1813;
13. h) for a review, see: P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953-2989.
14. a) R. Süess, A. Lindenmann, French Patent, FR 1549379, 1968 [Chem. Abstr. 1970, 72, 55428];
15. b) J. Morley, European Patent, EP 247971 A2, 1987 [Chem. Abstr. 1988, 109, 116055];
16. c) D. Flockerzi, V. Figala, H. Amschler, G. Hummel, German Patent, DE 4217401 A1, 1993 [Chem. Abstr. 1993, 118, 254760].
17. a) A. Lindenmann, R. Süess, French Patent, FR 1542649, 1968 [Chem. Abstr. 1969, 71, 124400];
18. b) A. Lindenmann, R. Süess, French Patent, FR 6827, 1969 [Chem. Abstr. 1971, 74, 53760].
19. a) B. B. Snider, T. C. Harvey, Tetrahedron Lett. 1995, 36, 4587-4590;
20. b) F. Hughes, R. B. Grossman, Org. Lett. 2001, 3, 2911-2914;
21. c) P. Kelemen, J. Lugtenburg, B. Klumperman, J. Org. Chem. 2003, 68, 7322-7328;
22. d) T. C. Wabnitz, J. B. Spencer, Org. Lett. 2003, 5, 2141-2144;
23. e) T. C. Wabnitz, J.-Q. Yu, J. B. Spencer, Chem. Eur. J. 2004, 10, 484-493;
24. f) M. J. Lee, K. Y. Lee, J. N. Kim, Bull. Korean Chem. Soc. 2005, 26, 477-480;
25. g) S. Dörrenbacher, U. Kazmaier, S. Ruf, Synlett 2006, 547-550.
26. a) A. Rosiak, W. Frey, J. Christoffers, Eur. J. Org. Chem. 2006, 4044-4054;
27. b) A. Rosiak, J. Christoffers, Synlett 2006, 1434-1436.
28. a) D. G. Farnum, J. Org. Chem. 1963, 28, 870-872;
29. b) G. Kaufman, F. Cook, H. Shechter, J. Bayless, L. Friedman, J. Am. Chem. Soc. 1967, 89, 5736-5737;
30. c) L. A. Paquette, M. K. Scott, J. Am. Chem. Soc. 1972, 94, 6751-6759;
31. d) A. R. Chamberlin, E. L. Liotta, F. T. Bond, Org. Synth. 1983, 61, 141-146;
32. e) A. M. Zvonok, E. B. Okaev, Chem. Heterocycl. Compd. 1996, 32, 310-312;
33. f) for a review, see: R. H. Shapiro, Org. React. 1976, 23, 405-507.
34. a) M. F. Lipton, R. H. Shapiro, J. Org. Chem. 1978, 43, 1409-1413;
35. b) S. F. Martin, D. Daniel, R. J. Cherney, S. Liras, J. Org. Chem. 1992, 57, 2523-2525.
36. V. P. Miller, D. Y. Yang, T. M. Weigel, O. Han, H. W. Liu, J. Org. Chem. 1989, 54, 4175-4188.
37. a) P. Grammaticakis, C. R. Seances Acad. Sci., Ser. C 1967, 264, 2067-2070
38. [Chem. Abstr. 1967, 67, 108368];
39. b) R. J. Cremlyn, S. W. Ahmad, Egypt. J. Chem. 1985, 28, 529-538.
40. a) A. R. Chamberlin, J. E. Stemke, F. T. Bond, J. Org. Chem. 1978, 43, 147-154;
41. b) A. S. Kende, L. N. Jungheim, Tetrahedron Lett. 1980, 21, 3849-3852;
42. c) M. S. Addie, R. J. K. Taylor, ARKIVOC 2000, 5, 660-666;
43. d) for a review, see: A. R. Chamberlin, S. H. Bloom, Org. React. 1991, 39, 1-83.
44. N. J. Cusack, C. B. Reese, A. C. Risius, B. Roozpeikar, Tetrahedron 1976, 32, 2157-2162.
45. M. S. Passafaro, B. A. Keay, Tetrahedron Lett. 1996, 37, 429-432.
46. a) J. Habermann, S. V. Ley, J. S. Scott, J. Chem. Soc. Perkin Trans. 1 1998, 3127-3130;
47. b) R. Laudien, R. Mitzner, J. Chem. Soc. Perkin Trans. 2 2001, 2226-2229.
48. For a review, see: S. Escoubet, S. Gastaldi, M. Bertrand, Eur. J. Org. Chem. 2005, 3855-3873.
49. a) J. Christoffers, H. Scharl, W. Frey, A. Baro, Eur. J. Org. Chem. 2004, 2701-2706;
50. b) S. Kolczewski, S. Roever, P. Schnider, World Patent, WO 062784 A1, 2002 [Chem. Abstr. 2002, 137, 169546].
51. J. Christoffers, A. Mann, Chem. Eur. J. 2001, 7, 1014-1027.