Reaction of 2-methoxy-3H-azepine with NBS: Efficient synthesis of 2-substituted 2H-azepines

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3425-3436

  Cordonier, Christopher E J ^a   Satake, Kyosuke ^a   Atarashi, Mikihiko ^a   Kawamoto, Yousuke ^a   Okamoto, Hideki ^a   Kimura, Masaru ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; DERIVATIVES; ETHERS; PARAFFINS; PHENOLS; SULFUR COMPOUNDS;

ALKANETHIOL; ELECTROPHILIC SUBSTITUTION; N-BROMOSUCCINIMIDE (NBS); TRANSETHERIFICATION;

REACTION KINETICS;

2 METHOXY 3H AZEPINE; AZEPINE DERIVATIVE; N BROMOSUCCINIMIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ETHERIFICATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; THERMOSTABILITY;

EID: 17744378990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0500232     Document Type: Article

References (38)

1. (a) Albini, A.; Bettinetti, G.; Minoli, G. J. Am. Chem. Soc, 1991, 113, 6928-6934.
2. (b) Hamprecht, D.; Josten, J.; Steglich, W. Tetrahedron 1996, 52, 10883-10902.
3. (c) Jones, D. W.; Thornton-Pett, M. J. Chem. Soc., Perkin Trans. 1 1995, 809-815.
4. (d) Steglich, W.; Bauer, H.; Grosse-Bley, M.; Jeschke, R.; Josten, J.; Klein, J. J. Heterocycl. Chem. 1990, 27, 107-110.
5. (a) Spiteller, P.; Hamprecht, D.; Steglich, W. J. Am. Chem. Soc. 2001, 123, 4837-4838.
6. (b) Sterner, O.; Steffan, B.; Steglich, W. Tetrahedron 1987, 43, 1075-1082.
7. (a) Satake, K.; Okuda, R.; Hashimoto, M.; Fujiwara, Y.; Okamoto, H.; Kimura, M.; Morosawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 1753-1757.
8. (b) Satake, K.; Okuda, R.; Hashimoto, M.; Fujiwara, Y.; Watadani, I.; Okamoto, H.; Kimura, M.; Morosawa, S. J. Chem. Soc., Chem. Commun. 1991, 1154-1156.
9. (c) Satake, K.; Saitoh, H.; Kimura, M.; Morosawa, S. Heterocycles 1994, 38, 769-778.
10. Satake, K.; Kubota, Y.; Cordonier, C.; Okamoto, H.; Kimura, M. Angew. Chem., Int. Ed. 2004, 43, 736-738.
11. (a) Masaki, M.; Fukui, K.; Kita, J. Bull. Chem. Soc. Jpn. 1977, 50, 2013-2016.
12. (b) Kubota, Y.; Satake, K.; Ikui, R.; Okamoto, H.; Kimura, M. Bull. Chem. Soc. Jpn. 2003, 76, 805-811.
13. Satake, K.; Cordonier, C.; Kubota, Y.; Jin, Y.; Kimura, M. Heterocycles 2003, 60, 2211-2215.
14. Satake, K.; Tawada, Y.; Okamoto, H.; Kimura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2015-2017.
15. Doering, W. Von E.; Knox, L. H. J. Am. Chem. Soc. 1954, 76, 3203-3206.
16. Doering, W. Von E.; Knox, L. H. J. Am. Chem. Soc. 1957, 79, 352-356.
17. (a) Di Stefano, M.; Rosi, M.; Sgamellotti, A.; Negri, F. Chem. Phys. 2004, 302, 295-308.
18. (b) Di Stefano, M.; Rosi, M.; Sgamellotti, A.; Ascenzi, D.; Bassi, D.; Franceschi, P.; Tosi, P. J. Chem. Phys. 2003, 119, 1978-1985.
19. (c) Smith, D. A.; Bitar, J. J. Org. Chem. 1993, 58, 6-8.
20. (d) Batori, S.; Gompper, R.; Meier, J.; Wagner, H.-U. Tetrahedron 1988, 44, 3309-3318.
21. (a) Paul, I. C.; Johnson, S. M.; Paquette, L. A.; Barrett, J. H.; Haluska, R. J. J. Am. Chem. Soc. 1968, 90, 5023-5024.
22. (b) Paquette, L. A. J. Am. Chem. Soc. 1963, 85, 4053-4054.
23. (a) Reeves, L. W.; Shaddick, R. C.; Shaw, K. N. Can. J. Chem. 1971, 49, 3683-3691.
24. (b) Martin, M. L.; Ricolleau, G.; Poignant, S.; Martin, G. J. J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. (1972-1999) 1976, 182-186.
25. (a) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
26. (b) Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-5509.
27. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
28. (b) Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265-3269.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Yonemoto, T. Can. J. Chem. 1966, 44, 223-231.
31. (a) Konya, N.; Seko, S. Eur. Patent 1072589 (20010131), 2001.
32. (b) Van, T. N.; Kimpe, N. Tetrahedron 2000, 56, 7969-7973.
33. (c) Deagostino, A.; Tivola, P. B.; Prandi, C.; Venturello, P. Synlett 1999, 1841-1843.
34. (d) Wakamatsu, K.; Kigoshi, H.; Niiyama, K.; Niwa, H.; Yamada, K. Tetrahedron 1986, 42, 5551-5558.
35. (e) Pearson, A. J.; Ray, T. Tetrahedron Lett. 1986, 27, 3111-3114.
36. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
37. (a) Stevani, C. V.; Silva, S. M.; Baader, W. J. Eur. J. Org. Chem. 2000, 4037-4046.
38. (b) Rauhut, M. M. Acc. Chem. Res. 1969, 2, 80-87.