Continuous-flow microreactor multi-step synthesis of an aminonaphthalene derivative as starting material for the preparation of novel anticancer agents

Arkivoc

Volumn 2008, Issue 8, 2008, Pages 193-210

  Tietze, Lutz F ^a   Liu, Deshan ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Biphasic reactions; Continuous flow reaction; Curtius rearrangement; Friedel Crafts acylation; Microreactor; Olefination

Indexed keywords

EID: 44649171164     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.816     Document Type: Article

References (67)

1. (a) Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300.
2. (b) Hartung, A.; Keane, M. A.; Kraft, A. J. Org. Chem. 2007, 72, 10235.
3. (c) Sahoo, H. R.; Kralji, J. G.; Jensen, K. F. Angew. Chem. In. Ed. 2007, 46, 5704.
4. (d) Jähnisch, K.; Hessel, V.; Löwe, H.; Baerns, M. Angew. Chem. Int. Ed. 2004, 43, 406.
5. (e) Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.; Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58, 4735.
6. (a) Hessel, V.; Hardt, S.; Löwe, H.; Schönfeld, F. AIChE J. 2003, 49, 566.
7. (b) Song, H.; Tice, J. D.; Ismagilov, R. F. Angew. Chem. Int. Ed. 2003, 42, 767.
8. (c) Taghavi-Moghadam, S.; Kleemann, A.; Golbig, K. G. Org. Process Res. Dev. 2001, 5, 652.
9. (a) Hisamoto, H.; Saito, T.; Tokeshi, M.; Hibara, A.; Kitamori, T. Chem. Comm. 2001, 2662.
10. Panke, G.; Schwalbe, T.; Stirner, W.; Taghavi-Moghadam, S.; Wille, G. Synthesis 2003, 2827.
11. (a) Usutani, H.; Tomida, Y.; Nagaki, A.; Okamoto, H.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc. 2007, 129, 3406.
12. (b) Kawaguchi, T.; Miyata, H.; Ataka, K.; Mae, K.; Yoshida, J. Angew. Chem. Int. Ed. 2005, 44, 2413.
13. (c) Nagaki, A.; Togai, M.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J. J. Am. Chem. Soc. 2005, 127, 11666.
14. (a) Anderson, N. G. Org. Process Res. Dev. 2001, 5, 613.
15. (b) Jas, G.; Kirschning, A. Chem. Eur. J. 2003, 9, 5708.
16. (a) Bayer, T.; Himmler, K. Chem. Eng. Technol. 2005, 28, 285.
17. (b) Markowz, G.; Schirrmeister, S.; Albrecht, J.; Becker, F.; Schütte, R.; Caspary, K. J.; Klemm, E. Chem. Eng. Technol. 2005, 28, 459.
18. (c) Chambers, R. D.; Fox, M. A.; Holling, D.; Nakano, T.; Okazoe, T.; Sandford, G. Chem. Eng. Technol. 2005, 28, 344.
19. (d) Hessel, V.; Hofmann, C.; Löwe, H.; Meudt, A.; Scherer, S.; Schönfeld, F.; Werner, B. Org. Process Res. Dev. 2004, 8, 511.
20. (e) Wakami, H.; Yoshida, J. Org. Process Res. Dev. 2005, 9, 787.
21. (f) Haswell, S. J.; Watts, P. Green Chem. 2003, 5, 240.
22. (a) Geyer, K.; Codée, J. D. C.; Seeberger, P. H. Chem. Eur. J. 2006, 12, 8434.
23. (b) Wörz, O.; Jäckel, K.; Richter, T.; Wolf, A. Chem. Eng. Technol. 2001, 24, 138.
24. (a) Roberge, D. M.; Ducry, L.; Bieler, N.; Cretton, P.; Zimmermann, B. Chem. Eng. Technol. 2005, 28, 318-323.
25. (b) Jensen, K. F. Chem. Eng. Sci. 2001, 56, 293.
26. (a) Flögel, O.; Codée, J. D. C.; Seebach, D.; Seeberger, P. H. Angew. Chem. Int. Ed. 2006, 45, 7000.
27. (b) Schwalbe, T.; Kadzimirsz, D.; Jas, G. QSAR Comb. Sci. 2005, 24, 758.
28. (c) Schwalbe, T.; Taghavi-Moghadam, S.; Rüger, R. Eur. Pat. Appl. EP 1160241-A2, 2001.
29. (a) Tietze, L. F.; Major, F.; Schuberth, I.; Spiegl, D. A.; Krewer, B.; Maksimenka, K.; Bringmann, G.; Magull, J. Chem. Eur. J. 2007, 13, 4396.
30. (b) Tietze, L. F.; Major, F.; Schuberth, I. Angew. Chem. Int. Ed. 2006, 45, 6574.
31. (a) Major, F. Dissertation, University of Göttingen, 2006.
32. (b) Chen, X. Dissertation, University of Göttingen, 2007; see also other syntheses of analogs of compound 1.
33. (c) Boger, D. L.; McKie, J. A.; Cai, H.; Cacciari, B.; Baraldi, P. G. J. Org. Chem. 1996, 61, 1710.
34. (d) Boger, D. L.; Han, N.; Tarby, C. M.; Boyce, C. W.; Cai, H.; Jin, Q.; Kitos, P. A. J. Org. Chem. 1996, 61, 4894.
35. (e) Jia, G.; Lown, J. W. Bioorg. Med. Chem. 2000, 8, 1607.
36. CYTOS® microreactor system was developed by CPC-Systems (Schwalbe, T.; Golbig, K.; Hohmann, M.; Georg, P.; Oberbeck, A.; Dittmann, B.; Stasna, J.; Oberbeck, S. Eur. Pat. Appl. EP 1123734, 2001) and its features was introduced in Ref. [2c].
37. See also its application for chemical synthesis: (a) Acke, D. R. J.; Stevens, C. V. Org. Process Res. Dev. 2006, 10, 417.
38. (b) Liu, S.; Fukuyama, T.; Sato, M.; Ryu, I. Org. Process Res. Dev. 2004, 8, 477.
39. (c) Zhang, X.; Stefanick, S.; Villani, F. J. Org. Process Res. Dev. 2004, 8, 455.
40. (d) Ref. [4]
41. (a) Abramovitch, B.; Shivers, J. C.; Hudson, B. E.; Hauser, C. R. J. Am. Chem. Soc. 1943, 65, 986.
42. (b) Vollmar, A.; Dunn, M. S. J. Org. Chem. 1960, 25, 387.
43. Schneider, D. F.; Viljoen, M. S. Synth. Commun. 2002, 32, 721.
44. (a) Gallagher, P. T.; Hicks, T. A.; Lightfoot, A. P.; Owton, W. M. Tetrahedron Lett. 1994, 35, 289.
45. (b) Owton, W. M.; Gallagher, P. T.; Juan-Montesinos, A. Synth. Commun. 1993, 23, 2119.
46. (a) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
47. (b) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
48. (a) Wadsworth, W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733-1738.
49. (b) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87.
50. Linke, S.; Kurz, J.; Lipinski, D.; Gau, W. Liebigs Ann. Chem. 1980, 542.
51. Mehta, A.; Jaouhari, R.; Benson, T. J.; Douglas, K. T. Tetrahedron Lett. 1992, 33, 5441.
52. (a) Boger, D. L.; Turnbull, P. J. Org. Chem. 1998, 63, 8004.
53. (b) Comber, M. F.; Sargent, M. V. J. Chem. Soc. Perkin Trans. 1 1991, 2783.
54. (c) Hughes, A. B.; Sargent, M. V. J. Chem. Soc. Perkin Trans. 1 1989, 449.
55. (d) Rizzacasa, M. A.; Sargent, M. V. Aust. J. Chem. 1987, 40, 1737.
56. (e) Borsche, W. Justus Liebigs Ann. Chem. 1936, 526, 1.
57. (a) Couladouros, E. A.; Strongilos, A. T. Eur. J. Org. Chem. 2002, 3341.
58. (b) Howell, F. H.; Taylor, D. A. H. J. Chem. Soc. 1956, 4252.
59. (a) Adams, S. P.; Whitlock, H. W. J. Org. Chem. 1981, 46, 3474.
60. (b) Roush, W. R.; Coffey, D. S.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 11331.
61. (c) Roush, W. R.; Madar, D. J. Tetrahedron Lett. 1993, 34, 1553.
62. 2H).
63. Ripin, D. H. B.; Vetelino, M. Synlett 2003, 2353.
64. (a) Ahmed, B.; Barrow, D.; Wirth, T. Adv. Synth. Catal. 2006, 348, 1043.
65. (b) Ueno, M.; Hisamoto, H.; Kitamori, T.; Kobayashi, S. Chem. Comm. 2003, 936.
66. (a) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151.
67. (b) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.