Preparation of 8-amido-2-dimethylamino-1,2,3,4-tetrahydro-2-dibenzofurans and several fluorinated derivatives via [3,3]-sigmatropic rearrangement of O-aryloximes

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 770-778

  Guzzo, Peter R ^a   Buckle, Ronald N ^a   Chou, Ming ^a   Dinn, Sean R ^a   Flaugh, Michael E ^b   Kiefer Jr , Anton D ^b   Ryter, Kendal T ^a   Sampognaro, Anthony J ^a   Tregay, Steven W ^a   Xu, Yao Chang ^b  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DERIVATIVES; SYNTHESIS (CHEMICAL);

DIFLUORINATED ANALOGUES;

FLUORINE CONTAINING POLYMERS;

8 AMIDO 2 DIMETHYLAMINO 1,2,3,4 TETRAHYDRO 2 DIBENZOFURAN; ANTIMIGRAINE AGENT; FLUOROBENZENE; N (3 DIMETHYLAMINO 2,3,4,9 TETRAHYDRO 1H CARBAZOL 6 YL) 4 FLUOROBENZAMIDE; SEROTONIN 1 AGONIST; SEROTONIN 1F RECEPTOR; TETRAHYDRODIBENZOFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; FLUORINATION; MIGRAINE; PROTON NUCLEAR MAGNETIC RESONANCE; SEROTONINERGIC SYSTEM;

CARBAZOLES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; FLUOROBENZENES; FURANS; HYDROCARBONS, FLUORINATED; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIMES; SEROTONIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037423260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020600b     Document Type: Article

References (33)

1. Hoyer, D.; Clarke, D. E.; Fozard, J. R.; Hartig, P. R.; Martin, G. R.; Mylecharane, E. J.; Saxena, P. R.; Humphrey, P. P. A. Pharmacol. Rev. 1994, 46, 157.
2. (a) Phebus, L. A.; Johnson, K. W.; Zgombick, J. M.; Gilbert, P. J.; Van Belle, K.; Mancuso, V.; Nelson, D. L. G.; Calligaro, D. O.; Kiefer, A. D.; Branchek, T. A.; Flaugh, M. E. Life Sci. 1997, 61, 2117.
3. (b) Johnson, K. W.; Schaus, J. M.; Durkin, M. M.; Audia, J. E.; Kaldor, S. W.; Flaugh, M. E.; Adham, N.; Zgombick, J. M.; Cohen, M. L.; Branchek, T. A.; Phebus, L. A. Neuroreport 1997, 8, 2237.
4. (c) Xu, Y.C.; Johnson, K. W.; Phebus, L. A.; Cohen, M.; Nelson, D. L.; Schenck, K.; Walker, C. D.; Fritz, J. E.; Kaldor, S. W.; LeTourneau, M. E.; Murff, R. E.; Zgombick, J. M.; Calligaro, D. O.; Audia, J. E.; Schaus, J. M. J. Med. Chem. 2001, 44, 4031.
5. (a) Flaugh, M. E.; Kiefer, A. D. U.S. Patent 5,846,995, December 8, 1998.
6. (b) Flaugh, M. E.; Kiefer, A. D. U.S. Patent 5,932,739, August 3, 1999.
7. (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991.
8. (b) Selective Fluorination; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991.
9. (c) Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207.
10. (a) Blair, J. B.; Kurrasch-Orbaugh, D.; Marona-Lewicka, D.; Cumbay, M. G.; Watts, V. J.; Barker, E. L.; Nichols, D. E. J. Med. Chem. 2000, 43, 4701.
11. (b) Laban, U.; Kurrasch-Orbaugh, D.; Marona Lewicka, D.; Nichols, D. E. Bioorg. Med. Chem. Lett. 2001, 11, 793.
12. Herbert, B.; Kim, I. H.; Kirk, K. L. J. Org. Chem. 2001, 66, 4892.
13. (a) Sheradsky, T. Tetrahedron Lett. 1966, 5225.
14. (b) Sheradsky, T. J. Heterocycl. Chem. 1967, 4, 413.
15. (c) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441.
16. (d) Mooradian, A. Tetrahedron Lett. 1967, 407.
17. (e) Kaminsky, D.; Shavel, J.; Meltzer, R. I. Tetrahedron Lett. 1967, 859.
18. (f) Mooradian, A.; Dupont, P. E. Tetrahedron Lett. 1967, 2867.
19. (g) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1984, 49, 4399.
20. (h) Alemagna, A.; Baldoli, C.; Buttero, P. D.; Licandro, E.; Maiorana, S. Synthesis 1987, 192.
21. (i) Liao, Y.; Kozikowski, A. P.; Guidotti, A.; Costa, E. Bioorg. Med. Chem. Lett. 1998, 8, 2099.
22. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1998, 110, 1496.
23. (a) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1984, 49, 1348.
24. (b) Choong, I. C.; Ellman, J. A. J. Org. Chem. 1999, 64, 6528.
25. (c) Foot, O. F.; Knight. D. W. Chem. Commun. 2000, 975.
26. Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139.
27. Baldoli, C.; Buttero, P. D.; Licandro, E.; Maiorana, S. Synthesis 1988, 344.
28. Mukai, C.; Nomura, I.; Kataoka, O.; Hanaoka, M. Synthesis 1999, 1872.
29. Flaugh, M. E.; Mullen, D. L.; Fuller, R. W.; Mason, N. R. J. Med. Chem. 1988, 31, 1746.
30. For a review of the Fischer Indole reaction see: Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607.
31. Wells, K. M.; Shi, Y.-J.; Lynch, J. E.; Humphrey, G. R.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1996, 37, 6439.
32. Marriott, J. H.; Moreno Barber, A. M.; Hardcastle, I. R.; Rowlands, M. G.; Grimshaw, R. M.; Neidle, S.; Jarman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2465 and references contained therein.
33. Paudler, W. W. Nuclear Magnetic Resonance General Concepts and Applications; John Wiley & Sons: New York, 1987.