SNAr-based, facile synthesis of a library of benzothiaoxazepine-1,1′-dioxides

Journal of Combinatorial Chemistry

Volumn 12, Issue 6, 2010, Pages 850-854

  Rolfe, Alan ^a   Samarakoon, Thiwanka B ^a   Klimberg, Sarra V ^a   Brzozowski, Marek ^a   Neuenswander, Benjamin ^a   Lushington, Gerald H ^a   Hanson, Paul R ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

OXAZEPINE DERIVATIVE; OXIDE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; MOLECULAR LIBRARY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; OXAZEPINES; OXIDES; SMALL MOLECULE LIBRARIES; THIAZOLES;

EID: 78149290306     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc1001023     Document Type: Article

References (30)

1. For reviews concerning ROMP reagents, see
2. Barrett, A. G. M., Hopkins, B. T., and Köbberling, J. Chem. Rev 2002, 102, 3301-3324
3. Flynn, D. L., Hanson, P. R., Berk, S. C., and Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 571-579
4. Harned, A. M., Probst, D. A., and Hanson, P. R. The Use of Olefin Metathesis in Combinatorial Chemistry: Supported and Chromatography-Free Syntheses. In Handbook of Metathesis; Grubbs, R. H., Ed.: Wiley-VCH: Weinheim, Germany, 2003; pp 361-402.
5. Harned, A. M., Zhang, M., Vedantham, P., Mukherjee, S., Herpel, R. H., Flynn, D. L., and Hanson, P. R. Aldrichimica Acta 2005, 38, 3-16
6. Nicolaou, K. C. and Chen, J. S. Chem. Soc. Rev. 2009, 11, 2993-3009
7. Enders, D., Grondal, C., and Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581
8. Tietze, L. F. and Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163
9. Tietze, L. F., Brasche, G., and Gericke, K. M., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
10. Rolfe, A., Young, K., and Hanson, P. R. Eur. J. Org. Chem. 2008, 5254-5262
11. Drews, J. Science 2000, 287, 1960-1964
12. Scozzafaa, A., Owa, T., Mastrolorenzo, A., and Supuran, C. T. Curr. Med. Chem. 2003, 10, 925-953
13. Zhuang, L., Wai, J. S., Embrey, M. W., Fisher, T. E., Egbertson, M. S., Payne, L. S., Guare, J. P., jr., Vacca, J. P., Hazuda, D. J., Felock, P. J., Wolfe, A. L., Stillmock, K. A., Witmer, M. V., Moyer, G., Schleif, W. A., Gabryelski, L. J., Leonard, Y. M., Lynch, J. J., Jr., Michelson, S. R., and Young, S. D. J. Med. Chem. 2003, 46, 453-456
14. Levy, L. Drugs Future 1992, 17, 451-454
15. Rabasseda, X. and Hopkins, S. L. Drugs Today 1994, 30, 557-563
16. Hendrick, R. T., Spencer, S. R., Blake, J. F., Fell, J. B., Fischer, J. P., Stengel, P. J., Leveque, V. J. P., LePogam, S., Rajyaguru, S., Najera, I., Joesy, J. A., and Swallow, S. Bioorg. Med. Chem. Lett. 2009, 19, 410-414
17. Valente, C., Guedes, R. C., Moreira, R., Iley, J., Gut, J., and Rosental, P. J. Biorg. Med. Chem. Lett. 2006, 16, 4115-4119
18. Misu, Y. and Togo, H. Org. Biomol. Chem. 2003, 1, 1342-1346
19. Rogers, K. and Patzke, H. U.S. Patent 0050,545P Nov 12, 2005.
20. Campbell, L., Pike, K. G., Suleman, A., and Waring, M. J. W.O.Patent 050,101 May 2, 2008.
21. Matsumoto, T., Kamo, I., and Nomura, I. W.O. Patent 8,007,661 Jan 17, 2008.
22. Santora, V. J., Covel, J. A., Ibarra, J. B., Semple, G., Smith, B., Smith, J., Weinhouse, M. I., and Schultz, J. A. W.O. Patent 8, 097, 261 Jan 10, 2008.
23. Fotouhi, N., Haley, G. J., Simonsen, K. B., Vu, B. T., and Webber, S. E. W.O. Patent 6,097,261 Sep. 21, 2006.
24. Askew, jr., B. C., Aya, T., Biswas, K., Cai, G., Chen, J. J., Fotsch, C. H., Han, N., Human, J. B., Li, A., Liu, Q., Peterkin, T., Qian, W., Riahi, B., Yuan, C. C., and Zhu, J. W.O. Patent 6,036,664 Apr 6, 2006
25. Grove, S. J. A., Zhang, M., and Shahid, M. W.O. Patent 2,100,865 Dec 19, 2002.
26. Duan, J., Chen, L., Cherney, R. J., Decicco, C. P., and Voss, M. E.; W.O. Patent 1, 994, 126 Aug 19, 1988.
27. Rolfe, A., Samarakoon, T. B., and Hanson, P. R. Org. Lett. 2010, 12, 1216-1219
28. Rolfe, A., Probst, D., Volp, K. A., Omar, I., Flynn, D., and Hanson, P. R. J. Org. Chem. 2008, 73, 8785-8790
29. 50 to form an activated species and hence would be scavenged by it from the crude reaction mixture, see ref 19.
30. Grubbs, R. H. and Rosen, R. K. Organometallics 1996, 15, 1518-1520