Novel synthesis of dibenzo[b,g] 1,5-oxazocines

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5827-5830

  Ouyang, Xiaohu ^a   Kiselyov, Alexander S ^a  

^a AMGEN INC   (United States)

Author keywords

Aza compounds; Supported reactions; Supposed reagents

Indexed keywords

CHLORPROMAZINE; DIBENZO[B,G][1,5]OXAZOCINE; HETEROCYCLIC COMPOUND; IMIPRAMINE; MACROCYCLIC COMPOUND; OXAZOCINE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ARTICLE; BROMINATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0033529965     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01150-8     Document Type: Article

References (38)

1. (a)Mueller, A. L.; Moe, S. T. US Patent 1997, 873011;
2. (b)Vermeulin, N. M. J.; O'Day, C. L.; Webb, H. K.; Burns, M. R.; Bergstrom, D. E. US Patent 1998, 85538;
3. (c)Averback, P.; Ghanbari, H.; Beheshti, I.; Morse, D. US Patent 1997, 858343;
4. (d)Haddjeri, N.; Blier, P.; De Montigny, C. J. Neurosci. 1998, 18, 10150;
5. (e)Kuo, C. Biophys. J. 1998, 75, 2845;
6. (f)Ocharan, M. E.; Asbun, J.; Valencia, I.; Castillo, C.; Castillo, E. F. Proc. West. Pharmacol. Soc. 1998, 41, 141; Gallego,M.; Casis, L.; Casis, O. Eur. J. Pharmacol. 1998, 360;
7. (f)Ocharan, M. E.; Asbun, J.; Valencia, I.; Castillo, C.; Castillo, E. F. Proc. West. Pharmacol. Soc. 1998, 41, 141; Gallego, M.; Casis, L.; Casis, O. Eur. J. Pharmacol. 1998, 360;
8. (g)Jagadeesh, S. R.; Subhash, M. N. Biol. Psychiatry 1998, 44, 617;
9. (h)Adali, O.; Carver, G. C.; Philpot, R. M. Arch. Biochem. Biophys. 1998, 358, 92;
10. (i)Casis, O.; Sanchez-Chapula, J. A. J. Cardiovasc. Pharmacol. 1998, 32, 521;
11. (j)Zhu, J.; Mix, E.; Bengtsson, B.-O.; Link, H. J. Peripher. Nerv. Syst. 1997, 2, 30;
12. (k)Muraoka, S.; Kamei, K.; Muneoka, K.; Takigawa, M. J. Neurochem. 1998, 71, 1709;
13. (l)Boyer, P.-A.; Skolnick, P.; Fossom, L. H. J. Mol. Neurosci. 1998, 10, 219;
14. (m)Wuonola, M.; Palfreyman, M. G.; Motohashi, N.; Kawase, M.; Gabay, S.; Gupta, R. R.; Molnar, J. Anticancer Res. 1998, 18, 337;
15. (n)Pajeva, I.; Wiese, M. J. Med. Chem. 1998, 41, 1815.
16. (a)Joergensen, T. K.; Andersen, K. E.; Andersen, H. S.; Hohlweg, R.; Madsen, P.; Olsen, U. B. Dutch Patent 96-DK 138 960401; CA 1996, 713004;
17. (b)Ohgoh, T.; Tanaka, S.; Fujimoto, M.; Kitahara, A. Yakugaku Zassi 1977, 97, 24;
18. (c)Gellatly, R. P.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans, 1 1976, 913;
19. (d)Tanaka, S.; Hashimoto, K. Yakugaku Zassi 1973, 93, 1003.
20. (a)Tanaka, S.; Hashimoto, K. Japan Patent JP 690908; CA 1972, 59680;
21. (b)Tanaka, S.; Hashimoto, K.; Watanabe, H.; Sakaguchi, K. Chem. Pharm. Bull. 1973, 21, 1683;
22. (c)Tanaka, S.; Hashimoto, K. US Patent 1974, 3,803,143;
23. (d)Lieb, F.; Eiter, K. Liebigs Ann. Chem. 1976, 14, 203;
24. (e)Tanaka, S.; Ogata, Y. Yakugaku Zassi 1972, 93, 1003.
25. NAr see, for example: (a)Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991, Chapter 1.
26. (b)Artamkina, G. A.; Egorov, M. P.; Beletskaya, I. P. Chem. Rev. 1982, 82, 427.
27. (a)Boger, D. L.; Yohannes, D.; Zhou, J.; Patane, M. A. J. Am. Chem. Soc. 1993, 115, 3420;
28. (b)Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721;
29. (c)Zhu, J. Synlett 1997, 133 and references cited therein;
30. (d)Gonzalez, G. I.; Zhu, J. P. J. Org. Chem. 1997, 62, 7544;
31. (e)Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnowsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419;
32. (f)Evans, D. A.; Dinsmore, C. J.; Ratz, A. M.; Evrard, D. A.; Barrow, J. C. J. Am. Chem. Soc. 1997, 119, 3417;
33. (g)Kiselyov, A. S.; Eisenberg, S.; Luo, Y. Tetrahedron 1998, 54, 10635;
34. (h)Kiselyov, A. S.; Eisenberg, S.; Luo, Y. Tetrahedron Lett. 1999, 40, 2465.
35. Ouyang, X.; Tamayo, N.; Kiselyov, A. S. Tetrahedron 1999, 55, 2827.
36. 2 afforded the expected amino acid in only a 7% yield. Additionally, attempts to conduct a second reductive amination of the resultant resin with 2-fluoro-5-nitrobenzaldehyde were unsuccessful under a variety of experimental conditions. However, changing the reductive amination sequence proved to be successful.
37. +), found: 271.1081.
38. +), found: 283.1445.