Biologically Active Compounds through Catalysis: Efficient Synthesis of N-(Heteroarylcarbonyl)-N′-(arylalkyl)piperazines

Chemistry - A European Journal

Volumn 10, Issue 3, 2004, Pages 746-757

  Kumar, Kamal ^a   Michalik, Dirk ^a   Castro, Ivette Garcia ^a   Tillack, Annegret ^a   Zapf, Alexander ^a   Arlt, Michael ^b   Heinrich, Timo ^b   Böttcher, Henning ^b   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b MERCK KGAA   (Germany)

Author keywords

Amphetamines; Carbonylation; Homogeneous catalysis; Hydroamination; Palladium

Indexed keywords

CARBON MONOXIDE; CATALYSIS; DRUG PRODUCTS; NEUROLOGY; STYRENE; SYNTHESIS (CHEMICAL);

DEBENZYLATION; HYDROAMINATION;

BIOCHEMISTRY;

AMINE; AROMATIC COMPOUND; BASE; CARBON MONOXIDE; HALIDE; HETEROCYCLIC COMPOUND; PALLADIUM; PIPERAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; SEROTONIN 2A ANTAGONIST; STYRENE;

ADDITION REACTION; AMINATION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CENTRAL NERVOUS SYSTEM; DEBENZYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS;

AMINATION; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; PIPERAZINES; RECEPTOR, SEROTONIN, 5-HT2A; SEROTONIN ANTAGONISTS;

EID: 1242307864     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305327     Document Type: Article

References (65)

1. a) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995;
2. b) F. Diederich, P. J. Stang, Metal Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998;
3. c) M. Beller, C. Bolm, Transition Metals for Organic Synthesis, Wiley-VCH, Weinheim, 1998.
4. H.-U. Blaser, F. Spindler, M. Studer, Appl. Catal. A 2001, 221, 119.
5. a) H. Böttcher, H. Greiner, J. Harting, G. Bartoszyk, C. Seyfried, C. van Amsterdam (Merck Patent GmbH, Germany), DE 19934433, 2001;
6. b) H. Böttcher, G. Bartoszyk, J. Harting, C. van Amsterdam, C. Seyfried (Merck Patent GmbH, Germany), DE 10102053, 2002;
7. c) H. Crassier, H. Böttcher, U. Eckert, A. Bathe, S. Emmert (Merck Patent GmbH, Germany), DE 10102944, 2002.
8. H. Böttcher, J. Marz, H. Greiner, J. Harting, G. Bartoszyk, C. Seyfried, C. van Amsterdam (Merck Patent GmbH, Germany), WO 2001007434, 2001.
9. H. Akgun, U. Hollstein, L. Hurwite, J. Pharm. Sci. 1988, 77, 735 and references therein.
10. a) H. Böttcher, R. Gericke, Liebigs Ann. Chem. 1988, 749;
11. b) A. Kasahara, T. Izumi, S. Murakami, K. Miyamato, T. Hino, J. Heterocycl. Chem. 1989, 26, 1405;
12. b) G. S. Ponticello, J. J. Baldwin, J. Org. Chem. 1979, 44, 4003;
13. c) H. Singer, W. Shive, J. Am. Chem. Soc. 1955, 77, 5700.
14. a) S. W. Pelletier, Chemistry of Alkaloids, Van Nostrand-Reinhold; New York, 1970;
15. b) C. D. Leake, The Amphetamines: Their Actions and Uses, Charles C. Thomas Co.: Springfield, 1958;
16. c) B. Testa, B. Salvesen, J. Pharm. Sci. 1980, 69, 497;
17. d) R. Laske, W. Meindl, E. Holler, H. Schönenberger, Arch. Pharm. 1989, 322, 297, 847;
18. th Ed., Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1996.
19. a) R. A. Glennon, M. Y. Yousif, A. M. Ismaiel, M. B. El-Ashmawy, J. L. Herndon, J. B. Fischer, A. C. Server, K. J. B. Howie, J. Med. Chem. 1991, 34, 3360;
20. b) A. S. F. Ash, A. M. Creighton, W. R. Wragg, Chem. Abstr. 1964, 60, 12028c;
21. c) D. R. Maxwell, W. R. Wragg, Chem. Abstr. 1964, 60, 5522f;
22. d) A. S. F. Ash, A. M. Creighton, W. R. Wragg, Chem. Abstr. 1964, 61, 8326f;
23. e) A. Mentrup, E. O. Renth, K. Schromm, P. Danneberg, C. H. Boehringer, Chem. Abstr. 1973, 78, 97704d.
24. a) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795;
25. b) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579;
26. c) M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, J. Herwig, T. E. Müller, O. R. Thiel, Chem. Eur. J. 1999, 5, 1306;
27. d) M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, A. Zapf, T. E. Müller, J. Organomet. Chem. 1998, 566, 277;
28. e) M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller, Eur. J. Inorg. Chem. 1999, 1121.
29. a) W. Mägerlein, A. Indolese, M. Beller, J. Mol. Catal. 2000, 156, 213;
30. b) W. Mägerlein, A. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940; Angew. Chem. Int. Ed. 2001, 40, 2856;
31. b) W. Mägerlein, A. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940; Angew. Chem. Int. Ed. 2001, 40, 2856;
32. c) M. Beller, A. Zapf, W. Mägerlein, Chem. Eng. Technol. 2001, 24, 575;
33. d) A. Schnyder, M. Beller, G. Mehltretter, A. F. Indolese, T. Nsenda, M. Studer, J. Org. Chem. 2001, 66, 4311;
34. e) W. Mägerlein, A. F. Indolese, M. Beller, J. Organomet. Chem. 2002, 641, 30.
35. a) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157;
36. b) M. Beller, C. Breindl, Chemosphere 2001, 43, 21.
37. Reviews: a) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675;
38. b) M. Beller, T. E. Müller, in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, Vol. 2, p. 316;
39. c) R. Taube in Applied Homogeneous Catalysis with Organomattalic Compounds (Eds.: B. Cornils, W. Herrmann), Wiley-VCH, Weinheim, 1996, p. 507;
40. d) D. Roundhill, Chem. Rev. 1992, 92, 1.
41. a) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389;
42. a) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389;
43. b) M. Beller, C. Breindl, T. H. Riermeier, A. Tillack, J. Org. Chem. 2001, 66, 1403;
44. c) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359;
45. d) D. Tzalis, C. Koradin, P. Knochel, Tetrahedron Lett. 1999, 40, 6193;
46. e) J. A. Seijas, M. P. Vázques-Tato, M. M. Martínez, Tetrahedron Lett. 1998, 39, 5073;
47. f) J. A. Seijas, M. P. Vázques-Tato, M. M. Martínez, Synlett 2001, 875;
48. g) R. J. Schlott, J. C. Falk, K. W. Narducy, J. Org. Chem. 1972, 37, 4243;
49. h) R. Wegler, G. Pieper, Chem. Ber. 1950, 83, 1.
50. For recent reviews on automated synthesis technologies in organic chemistry see: a) J. Yoshida, S. Suga, K. Itami, Kagaku Kogyo 2002, 53, 6;
51. b) S. V. Ley, I. R. Baxendale, Nat. Rev. Drug Discovery 2002, 1, 573;
52. c) T. Sugawara, J. Syn. Org. Chem. Jpn. 2002, 60, 465;
53. d) A. Hagemeyer, B. Jandeleit, Y. Liu, D. M. Poojary, H. W. Turner, A. F. Volpe, W. H. Weinberg, Appl. Catal. 2001, 221, 23.
54. Recent applications of automated synthesis to non-DNA chemistry: a) A. Jacobi von Wangelin, H. Neumann, D. Gördes, A. Spannenberg, M. Beller, T. Krüger, C. Wendler, K. Thurow, N. Stoll, Chem. Eur. J. 2003, 9, 2273;
55. b) R. G. Gentles, D. Wodka, D. C. Park, A. Vasudevan, J. Comb. Chem. 2002, 4, 442;
56. c) F. Schüth, O. Busch, C. Hoffmann, T. Johann, C. Kiener, D. Demuth, J. Klein, S. Schunk, W. Strehlau, T. Zech, Top. Catal. 2002, 21, 55;
57. d) M. S. Schiedel, C. A. Briehn, P. Bäuerle, J. Organomet. Chem. 2002, 653, 200.
58. a) D. Steinborn, R. Taube, Z. Chem. 1986, 26, 349;
59. b) H. M. Senn, P. E. Blöchl, A. Togni, J. Am. Chem. Soc. 2000, 122, 4098.
60. C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157.
61. a) V. K. Aggarwall, S. J. Roseblade, J. K. Barrell, R. Alexander, Org. Lett. 2002, 4, 1227;
62. b) For another example of Pd-catalyzed hydrogenolysis with triethylamine as an additive see: F. Effenberger, J. Jager, Chem. Eur. J. 1997, 3, 1370.
63. a) M. Beller, W. Mägerlein, A. F. Indolese, C. Fischer, Synthesis 2001, 1098;
64. b) M. Beller, A. F. Indolese, Chimia 2001, 55, 684.
65. For the pharmacological characterization of an analogue see: G. D. Bartoszyk, C. V. Amsterdam, H. Böttcher, C. A. Seyfried, Eur. J. Pharmacol. 2003, 473, 229.