New and efficient synthesis of 6,11-dihydro-11-ethyl-5H-dibenz[b,e]azepine derivatives starting from N-benzylanilines via amino-Claisen and Friedel-Crafts methodologies

Synlett

Volumn , Issue 15, 2004, Pages 2721-2724

  Palma, Alirio ^a   Barajas, Jacqueline Jaimes ^a   Kouznetsov, Vladimir V ^a   Stashenko, Elena ^a   Bahsas, Ali ^b   Amaro Luis, Juan ^b  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD DE LOS ANDES   (Venezuela)

Author keywords

Amino Claisen rearrangement; Dibenz b,e azepine derivatives; Intramolecular alkene Friedel Crafts alkylation; N allylation

Indexed keywords

6,11 DIHYDRO 11 ETHYL 5H DIBENZ[B,E]AZEPINE DERIVATIVE; ALKENE; ANILINE DERIVATIVE; BENZAZEPINE DERIVATIVE; BORON TRIFLUORIDE; N BENZYLANILINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; AMINO CLAISEN REARRANGEMENT; ARTICLE; CATALYSIS; CHEMICAL REACTION; CLAISEN REARRANGEMENT; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 10844277087     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-836026     Document Type: Article

References (28)

1. Briel, D. Pharmazie 1990, 45, 895.
2. Roeder, T.; Degen, J.; Gewecke, M. Eur. J. Pharmacol. 1998, 349, 171.
3. Sipido, V. K.; Fernández-Gadea, F. J.; Andrés-Gil, J. I.; Meert, T. F.; Gil-Lopetegui, P. PCT Int. Appl. WO 96 14320, 1996; Chem. Abstr. 1996, 125, 142705g.
4. Andrés, J. I.; Alcázar, J.; Alonso, J. M.; Díaz, A.; Fernández, J.; Gil, P.; Iturrino, L.; Matesanz, E.; Meert, T. F.; Megens, A.; Sipido, V. K. Bioorg. Med. Chem. Lett. 2002, 12, 243.
5. Andersen, K. E.; Olsen, U. B.; Andersen, H. S.; Hohlweg, R.; Joergensen, T. K.; Madsen, P. PCT Int. Appl. WO 96 31482, 1996; Chem. Abstr. 1997, 126, 8148v.
6. Joergensen, T. K.; Andersen, K. E.; Andersen, H. S.; Hohlweg, R.; Madsen, P.; Olsen, U. B. PCT Int. Appl. WO 96 31497, 1996; Chem. Abstr. 1997, 126, 8146t.
7. Brugnara, C.; Halperin, J.; Bellott, E. M. J. r.; Froimowitz, M.; Lombardy, R. J.; Clifford, J. J.; Gao, Y.-D.; Haidar, R. M.; Kelleher, E. W.; Kher, F. M.; Moussa, A. M.; Sachdeva, Y.; Sun, M.; Taft, H. N.; Lencer, W. I.; Alper, S. PCT Int. Appl. WO 99 26628, 1999; Chem. Abstr. 1999, 131, 18936t.
8. Fukumi, H.; Sakamoto, T.; Sugiyama, M.; Iizuka, Y.; Yamaguchi, T. U.S. US 5476848, 1995; Chem. Abstr. 1996, 1124, 261063k.
9. Sinha, A. K.; Nizamuddin, S. Ind. J. Chem., Sect. B 1984, 23, 83.
10. (a) Sasakura, K.; Sugasawa, T. Heterocycles 1981, 15, 421.
11. (b) Lypacewicz, M. K.; Poslinska-Bucewka, H.; Smolinska, J.; Wasiak, T.; Sosinska, D.; Mostrak, M.; Trzpil, B.; Paszkowski, S. Pol. PL 175287, 1998; Chem. Abstr. 1999, 130, 296698x.
12. (c) Stappers, F.; Broeckx, R.; Leurs, S.; Van den Bergh, L.; Agten, J.; Lambrechts, A.; Van den Heurel, D.; De Smaele, D. Org. Proc. Res. Develop. 2002, 6, 911.
13. (a) Moriconi, E. J.; Maniscalco, I. A. J. Org. Chem. 1972, 37, 208.
14. (b) Sinha, A. K.; Nizamuddin, S. Ind. J. Chem., Sect. B 1984, 23, 165.
15. Kouznetsov, V.; Palma, A. R.; Salas, S.; Vargas, L. Y.; Zubkov, F. I.; Varlamov, A. V.; Martínez, J. R. J. Heterocycl. Chem. 1997, 34, 1591.
16. Palma, A. R.; Rozo, W.; Stashenko, E.; Molina, D.; Kouznetsov, V. J. Heterocycl. Chem. 1998, 35, 183.
17. Kouznetsov, V.; Palma, A.; Rozo, W.; Stashenko, E.; Bahsas, A.; Arnaro-Luis, J. Tetrahedron Lett. 2000, 41, 6985.
18. Varlamov, A.; Kouznetsov, V.; Zubkov, F.; Chernyshev, A.; Alexandrov, G.; Palma, A.; Vargas, L.; Salas, S. Synthesis 2001, 849.
19. Palma, A.; Salas, S.; Kouznetsov, V.; Stashenko, E.; Montenegro, N. G.; Fontela, G. A. J. Heterocycl. Chem. 2001, 38, 837.
20. Kouznetsov, V.; Palma, A.; Rozo, W.; Stashenko, E.; Bahsas, A.; Aniaro-Luis, J. Synth. Commun. 2002, 32, 2965.
21. Baxter, E. W.; Labaree, D.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 7682.
22. Barta, N. S.; Cook, G. R.; Landis, M. S.; Stille, J. R. J. Org. Chem. 1992, 57, 7188.
23. Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849.
24. Stroh, R.; Ebersberger, J.; Haberland, H.; Hahn, W. Angew. Chem. 1957, 69, 124.
25. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
26. Anderson, W. K.; Lai, G. Synthesis 1995, 1287.
27. +], 256 (2), 242 (4), 194 (7), 180 (33), 166 (18), 145 (46), 130 (14), 115 (8), 91 (100), 77 (8), 65 (22).
28. 18ClN: C, 75.13; H, 6.68: N, 5.15. Found: C, 75.29; H, 6.83; N, 5.08.