Synthesis of substituted 4-amino-2-benzazepin-3-ones via N-acyliminium ion cyclizations

Synlett

Volumn , Issue 18, 2005, Pages 2791-2795

  Ballet, Steven ^a   Urbanczyk Lipkowska, Zofia ^b   Tourwé, Dirk ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

4 amino 1,2,4,5 tetrahydro 2 benzazepin 3 one template; Benzotriazole adducts; Friedel Crafts alkylation; N acyliminium ions

Indexed keywords

ALUMINUM CHLORIDE; BENZAZEPINE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; IMINE;

ACYLATION; ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; FRIEDEL CRAFTS REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 27844599690     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918946     Document Type: Article

References (31)

1. Examples given: (a) ACE inhibitors: Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914.
2. (b) NEP inhibitors: Warchawsky, A. M.; Flynn, G. A.; Koehl, J. R.; Mehdi, S.; Vaz, R. J. Bioorg. Med. Chem. Lett. 1996, 6, 957.
3. (c) Farnesyl transferase inhibitors: Le Duguarher, T.; Ortuno, J.-C.; Shanks, D.; Guilbaud, N.; Pierré, A.; Raimbaud, E.; Fauchère, J.-L.; Hickman, J. A.; Tucker, G. C.; Casara, P. J. Bioorg. Med. Chem. Lett. 2004, 14, 767.
4. th ACS Med. Chem. Meeting, San Francisco, 2000, Poster 192.
5. (e) Integrin antagonists: Miller, W. H.; AIi, F. E.; Bondinell, W. E.; Callahan, J. F.; Calvo, R. R.; Eggleston, D. S.; Haltiwanger, R. C.; Huffman, W. F.; Hwang, S.-M.; Jakas, D. R.; Keenan, R. M.; Koster, P. F.; Ku, T. W.; Kwon, C.; Newlander, K. A.; Nichols, A. J.; Parker, M. F.; Samanen, J. M.; Southall, L. S.; Takata, D. T.; Uzinskas, I. N.; Valocik, R. E.; Vasko-Moser, J. A.; Wong, A. S.; Yellin, T. O.; Yuan, C. C. K. Bioorg. Med. Chem. Lett. 1996, 6, 2481.
6. (f) Fibrinogen receptor antagonists: Keenan, R. M.; Callahan, J. F.; Samanen, J. M.; Bondinell, W. E.; Calvo, R. R.; Chen, L.; DeBrosse, C.; Eggleston, D. S.; Haltiwanger, R. C.; Hwang, S.-M.; Jakas, D. R.; Ku, T. W.; Miller, W. H.; Newlander, K. A.; Nichols, A.; Parker, M. F.; Southhall, L. S.; Uzinskas, I.; Vasko-Moser, J. A.; Venslavsky, J. W.; Wong, A. S.; Huffman, W. F. J. Med. Chem. 1999, 42, 545.
7. (g) Analgesics: Sawa, Y.; Takeshi, K.; Toru, M.; Mikio, H.; Hajime, F. Chem. Pharm. Bull 1975, 23, 1917.
8. (a) Flynn, G. A.; Burkholder, T. P.; Huber, E. W.; Bey, P. Bioorg. Med. Chem. Lett. 1991, 1, 309.
9. (b) Van Rompaey, K.; Van den Eynde, I.; De Kimpe, N.; Tourwé, D. Tetrahedron 2003, 59, 4421.
10. (c) Tourwé, D.; Verschueren, K.; Frycia, A.; Davis, P.; Porreca, F.; Hruby, V. J.; Toth, G.; Jaspers, H.; Verheyden, P.; Van Binst, G. Biopolymers 1995, 38, 1.
11. (d) Kouznetsov, V.; Palma, A.; Ewert, C. Curr. Org. Chem. 2001, 5, 519.
12. (e) Gámez-Montaño, R.; Chávez, M. I.; Roussi, G.; Cruz-Almanza, R. Tetrahedron Lett. 2001, 42, 9.
13. Katritzky, A. R.; Lan, X.; Zhang, Z. J. Heterocycl. Chem. 1993, 30, 381.
14. Katritzky, A. R.; Mehta, S.; He, H.-Y. J. Org. Chem. 2001, 66, 148.
15. Mecozzi, T.; Petrini, M.; Profeta, R. Tetrahedron: Asymmetry 2003, 14, 1171.
16. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989.
17. (a) N-Phthaloyl-(S)-phenylalanine was obtained following the methodology described by: Casimir, J. R.; Guichard, G.; Briand, J.-P. J. Org. Chem. 2002, 67, 3764.
18. 3.
19. Katritzky, A. R.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555.
20. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
21. Bose, A. J.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 34, 3167.
22. Srinivasan, N.; Ganesan, A. Chem. Commun. 2003, 916.
23. Kinderman, S. S.; Wekking, M. M. T.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 5519.
24. 2O gave compound 5 (entries 1-3) in quantitative yields.
25. 4 the solvent was removed in vacuo. Flash chromatography (15% EtOAc in hexanes) or crystallization (from EtOH) yielded compounds 8 (entries 1-5).
26. 2O (5 mL). Isolation of the organic phase, evaporation and flash chromatography yielded the benzazepinones 10 (entries 1-7).
27. 3): δ = 34.6, 52.7, 123.9, 126.9, 128.0, 128.0, 129.0, 129.7, 130.0, 131.0, 132.9, 134.5, 136.8, 139.3, 141.1, 167.8, 172.0.
28. 3): δ = 14.2 and 14.6, 33.7 and 34.6, 53.1, 52.3 and 54.0, 61.7 and 61.8, 69.3 and 70.4, 123.8, 126.9, 128.0, 129.0, 129.5, 130.3, 131.9, 134.5, 136.0, 137.5, 139.6, 139.3, 141.5, 169.2, 169.5, 170.1.
29. eq of the parent atom. The residual electron densities were of no chemical significance. Accordingly, CCDC-279757 [8 (entry 1)], and CCDC-279758 [10 (entry2)] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at http://www.ccdc.cam.ac. uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; e-mail: deposit@ccdc.cam.sc.uk).
30. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
31. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.