Substituted 1,4-benzoxazepines, 1,5-benzoxazocines, and N- and S-variants

Organic Letters

Volumn 11, Issue 23, 2009, Pages 5494-5496

  Rujirawanich, Janjira ^b   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b KASETSART UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449165873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9023453     Document Type: Article

References (37)

1. Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616.
2. Williams, A. J.; Chakthong, S.; Gray, D.; Lawrence, R. M.; Gallagher, T. Org. Lett. 2003, 5, 811-814.
3. Bower, J. F.; Švenda, J.; Williams, A. J.; Charmant, J. P. H.; Lawrence, R. M.; Szeto, P.; Gallagher, T. Org. Lett. 2004, 6, 4727-4730.
4. Bower, J. F.; Szeto, P.; Gallagher, T. Chem. Commun. 2005, 5793-5795.
5. Bower, J. F.; Chakthong, S.; Svenda, J.; Williams, A. J.; Lawrence, R. M.; Szeto, P.; Gallagher, T. Org. Biomol. Chem. 2006, 4, 1868-1877.
6. Bower, J. F.; Riis-Johannessen, T.; Szeto, P.; Whitehead, A. J.; Gallagher, T. Chem. Commun. 2007, 728-730.
7. Bower, J. F.; Szeto, P.; Gallagher, T. Org. Biomol. Chem. 2007, 5, 143-150.
8. Bower, J. F.; Szeto, P.; Gallagher, T. Org. Lett. 2007, 9, 4909-4912.
9. Bower, J. F.; Williams, A. J.; Woodward, H. L.; Szeto, P.; Lawrence, R. M.; Gallagher, T. Org. Biomol. Chem. 2007, 5, 2636-2644.
10. Nguyen, H. N.; Wang, Z. J. Tetrahedron Lett. 2007, 48, 7460-7463.
11. Xiong, Z. M.; Gao, D. H. A.; Cogan, D. A.; Goldberg, D. R.; Hao, M. H.; Moss, N.; Pack, E.; Pargellis, C.; Skow, D.; Trieselmann, T.; Werneburg, B.; White, A. Bioorg. Med. Chem. Lett. 2008, 18, 1994-1999.
12. Bandini, M.; Eichholzer, A.; Tragni, M.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2008, 47, 3238-3241.
13. So, S. M.; Yeom, C. E.; Cho, S. M.; Choi, S. Y.; Chung, Y. K.; Kim, B. M. Synlett 2008, 702-706.
14. Bower, J. F.; Szeto, P.; Gallagher, T. Org. Lett. 2007, 9, 3283-3286.
15. Congreve, M.; Carr, R.; Murray, C.; Jhoti, H. Drug Discovery Today 2003, 8, 876-877.
16. "Rule of three" is a fragment-based variant of Lipinski's "rule of five": Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25.
17. Lipinski, C. A. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
18. Examples of these heterocycles abound in the literature and in the patent literature. A recent example is BMS-214662, an enantiomerically pure 1,4-benzodiazepine that is a highly apotopic farnesyltransferase inhibitor displaying potent antitumor activity. Hunt, J. T.; Ding, C. Z.; Batorsky, R.; Bednarz, M.; Bhide, R.; Cho, Y.; Chong, S.; Chao, S.; GulloBrown, J.; Guo, P.; Kim, S. H.; Lee, F. Y. F.; Leftheris, K.; Miller, A.; Mitt, T.; Patel, M.; Penhallow, B. A.; Ricca, C.; Rose, W. C.; Schmidt, R.; Slusarchyk, W. A.; Vite, G.; Manne, V. J. Med Chem. 2000, 43, 3587-3595.
19. Reid, T. S.; Beese, L. S. Biochemistry 2004, 43, 6877-6884.
20. (a) Bellinger, A. M.; Mongillo, M.; Marks, A. R. J. Clin. Invest. 2008, 118, 445-453.
21. Bellinger, A. M.; Reiken, S.; Dura, M.; Murphy, P. W.; Deng, S. X.; Landry, D. W.; Nieman, D.; Lehnart, S. E.; Samaru, M.; LaCampagne, A.; Marks, A. R. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2198-2202.
22. Bellinger, A. M.; Reiken, S.; Carlson, C.; Mongillo, M.; Liu, X. P.; Rothman, L.; Matecki, S.; Lacampagne, A.; Marks, A. R. Nat. Medicine 2009, 15, 325-330.
23. 3 is that phenols, anilines, and thiophenols are effective nucleophiles towards a range of other and more substituted cyclic sulfamidates and that chemistry demonstrated with 4a/b and 10 is not limited in terms of its further application and scope. For this reason, our focus was on the range of heterocyclic scaffolds available rather than the substitution pattern associated with each individual substrate. In addition, the enantiomeric purity of adducts such as 6 and 7a-c is based on this earlier experience where loss of stereochemical integrity at a nonreacting center was never observed. By analogy, we have assumed that 12b derived from 10 is also a single enantiomer.
24. For recent examples of conventional (i.e., using acidic NH nucleophiles) Mitsunobu cyclizations to generate medium ring benzofused heterocycles, see: Banfi, L.; Guanti, A. B. G.; Lecinska, P.; Riva, R. Org. Biomol. Chem. 2006, 4, 4236-4240.
25. Banfi, L.; Basso, A.; Guanti, G.; Kielland, N.; Repetto, C.; Riva, R. J. Org. Chem. 2007, 72, 2151-2160.
26. For a very recent entry to benzoxazepines via an alternative (but related) double displacement, see: Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Org. Lett. 2009, 11, 257-260.
27. Mishra, J. K.; Panda, G. J. Comb. Chem. 2007, 9, 321-338. This group employed (i) an intermolecular Mitsunobu alkylation (using a 2-amino alcohol) and (ii) a Mitsunobu cyclization of an NHTs nucleophile to achieve medium ring formation. An example of a 1,4-benzodiazocine (compare the 1,5-isomer 12b described here) was also reported.
28. Sulfonyl migration from the aniline nitrogen to the other nitrogen center within the initial adduct (resulting from reaction of 4a with 5c) was observed. Varying amounts of sulfonyl migration (from the aniline moiety and depending on the workup conditions) also accompanied formation of 8b and lib. See Supporting Information.
29. Nikam, S. S.; Kornberg, B. E.; Rafferty, M. F. J. Org. Chem. 1997, 62, 3754-3757.
30. Pd-mediated amination has been successfully exploited to generate seven-membered rings. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed Engl. 1995, 34, 1348-1350.
31. Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
32. Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37.
33. Omar-Amrani, R.; Thomas, A.; Brenner, E.; Schneider, R.; Fort, Y. Org. Lett. 2003, 5, 2311-2314.
34. Qadir, M.; Priestley, R. E.; Rising, T.; Gelbrich, T.; Coles, S. J.; Hursthouse, M. B.; Sheldrake, P. W.; Whittall, N.; Hii, K. K. Tetrahedron Lett. 2003, 44, 3675-3678.
35. Omar-Amrani, R.; Schneider, R.; Fort, Y. Synthesis 2004, 2527-2534.
36. Kitamura, Y.; Hashimoto, A.; Yoshikawa, S.; Odaira, J.; Furuta, T.; Kan, T.; Tanaka, K. Synlett 2006, 115-117.
37. 2Et variants were evaluated without success. C-Br reduction (cf. 15) remained the major pathway observed for these ortho-bromo phenolic ethers in attempts to generate a sevenmembered ring.