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Publisher: American Chemical Society
Languages: English
Types: Article
Subjects:
A one-pot multibond-forming process involving a thermally mediated Overman rearrangement and a ring closing metathesis reaction of allylic trichloroacetimidates bearing a 2-allyloxyaryl group has been developed for the synthesis of 5-amino-substituted 2,5-dihydro-1-benzoxepines. Chemoselective reduction and functionalization of these compounds allowed access to a range of pharmacologically active 5-amino-2,3,4,5-tetrahydro-1-benzoxepine scaffolds.
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    • (1) (a) Engler, M.; Anke, T.; Sterner, O. J.; Brandt, U. J. J. Antibiot.
    • 1997, 50, 325. (b) Engler, M.; Anke, T.; Sterner, O. J. J. Antibiot. 1997, 50, 330.
    • (2) Bruder, M.; Haseler, P. L.; Muscarella, M.; Lewis, W.; Moody, C.
    • J. J. Org. Chem. 2010, 75, 353 and references therein.
    • (3) Wijnberg, J. B. P. A.; van Veldhuizen, A.; Swarts, H. J.; Frankland, J. C.; Field, J. A. Tetrahedron Lett. 1999, 40, 5767.
    • (4) Asakawa, Y.; Hashimoto, T.; Takikawa, K.; Tori, M.; Ogawa, S.
    • Phytochemistry 1991, 30, 235.
    • (5) Macias, F. A.; Molinillo, J. M. G.; Varela, R. M.; Torres, A.; Fronczek, F. R. J. Org. Chem. 1994, 59, 8261.
    • (6) Liu, G.; Lu, X. Adv. Synth. Catal. 2007, 349, 2247.
    • (7) Liu, J.; Liu, Y. Org. Lett. 2012, 14, 4742.
    • (8) Raju, B. C.; Saidachary, G.; Kumar, J. A. Tetrahedron 2012, 68, 6289.
    • (9) Yamaguchi, S.; Tsuchida, N.; Miyazawa, M.; Hirai, Y. J. Org.
    • Chem. 2005, 70, 7505.
    • (10) Jimeńez-Gonzaĺez, L.; García-Muñoz, S.; Álvarez-Corral, M.; Muñoz-Dorado, M.; Rodríguez-García, I. Chem.Eur. J. 2006, 12, 8762.
    • (11) For example, see: Kotha, S.; Mandal, K.; Tiwari, A.; Mobin, S.
    • M. Chem.Eur. J. 2006, 12, 8024.
    • (12) Stefinovic, M.; Snieckus, V. J. Org. Chem. 1998, 63, 2808. A slightly different strategy involving directed ortho metalation is used to install the initial allyl group in this paper.
    • (13) Yoshida, M.; Nakatani, K.; Shishido, K. Tetrahedron 2009, 65, 5702.
    • (14) (a) Swift, M. D.; Sutherland, A. Org. Lett. 2007, 9, 5239.
    • (b) Calder, E. D. D.; Grafton, M. W.; Sutherland, A. Synlett 2014, 25, 1068.
    • (15) (a) McGonagle, F. I.; Brown, L.; Cooke, A.; Sutherland, A. Org.
    • Biomol. Chem. 2010, 8, 3418. (b) Ahmad, S.; Sutherland, A. Org.
    • Biomol. Chem. 2012, 10, 8251.
    • (16) (a) Ahmad, S.; Swift, M. D.; Farrugia, L. J.; Senn, H. M.; Sutherland, A. Org. Biomol. Chem. 2012, 10, 3937. (b) Grafton, M. W.; Farrugia, L. J.; Senn, H. M.; Sutherland, A. Chem. Commun. 2012, 48, 7994. (c) Grafton, M. W.; Farrugia, L. J.; Sutherland, A. J. Org. Chem.
    • 2013, 78, 7199. (d) Grafton, M. W.; Johnson, S. A.; Farrugia, L. J.; Sutherland, A. Tetrahedron 2014, 70, 7133. (e) Calder, E. D. D.; McGonagle, F. I.; Harkiss, A. H.; McGonagle, G. A.; Sutherland, A. J.
    • Org. Chem. 2014, 79, 7633.
    • (17) For example, see: (a) Webster, R. A. B.; Cassidy, F. Benzoxepine and related compounds. Patent WO1989011477, November 30, 1989.
    • (b) Brendel, J.; Lang, H. J.; Gerlach, U. Sulfonamide-substituted fused 7-membered ring compounds, their use as a medicament, and pharmaceutical preparations comprising them. U.S. Patent US6333349 B1, December 25, 2001. (c) Deng, G. G.; Gavardinas, K.; Jadhav, P. K.; Kim, E. J.; Schiffler, M. A. Cathepsin S inhibitor compounds. U.S. Patent US20120095020 A1, April 19, 2012.
    • (18) Buckle, D. R.; Eggleston, D. S.; Houge-Frydrych, C. S. V.; Pinto, I. L.; Readshaw, S. A.; Smith, D. G.; Webster, R. A. B. J. Chem. Soc.
    • Perkin Trans. 1 1991, 2763.
    • (19) Nioche, J. Y.; Decerprit, J.; Festal, D. Eur. J. Med. Chem. 1995, 30, 377.
    • (20) Protiva, M.; Seidlova,́ V.; Svat́ek, E.; Hradil, F. Collect. Czech.
    • Chem. Commun. 1972, 37, 868.
    • (21) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masumune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
    • (22) Overman, L. E.; Carpenter, N. E. In Organic Reactions; Overman, L. E.; Ed.; Wiley: Hoboken, NJ, 2005; Vol. 66, 1−107 and references therein.
    • (23) (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew.
    • Chem., Int. Ed. 1995, 34, 2039. (b) Schwab, P.; Grubbs, R. H.; Ziller, J.
    • W. J. Am. Chem. Soc. 1996, 118, 100.
    • (24) (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett.
    • 1999, 1, 953. (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am.
    • Chem. Soc. 2001, 123, 6543.
    • (25) Carey, J. S.; MacCormick, S.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Org. Biomol. Chem. 2011, 9, 3896.
    • (26) (a) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem.
    • 1992, 57, 2497. (b) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R.
    • Tetrahedron Lett. 1993, 34, 3389.
    • (27) (a) Hamilton, D. J.; Sutherland, A. Tetrahedron Lett. 2004, 45, 5739. (b) Bischoff, R.; McDonald, N.; Sutherland, A. Tetrahedron Lett.
    • 2005, 46, 7147. (c) Reid, C. M.; Ebikeme, C.; Barrett, M. P.; Patzewitz, E.-M.; Müller, S.; Robins, D. J.; Sutherland, A. Bioorg. Med.
    • Chem. Lett. 2008, 18, 5399. (d) Zaed, A. M.; Sutherland, A. Org.
    • Biomol. Chem. 2010, 8, 4394. (e) Blair, A.; Stevenson, L.; Sutherland, A. Tetrahedron Lett. 2012, 53, 4084.
    • (28) (a) Rich, D. H. In Comprehensive Medicinal Chemistry, Sammes, P. G. ; Ed.; Pergamon Press: Oxford, 1990; Vol. 2, 391. (b) Bergmeier, S. C. Tetrahedron 2000, 56, 2561 and references therein.
    • (29) (a) Donohoe, T. J.; Blades, K.; Helliwell, M.; Moore, P. R.; Winter, J. J. G. J. Org. Chem. 1999, 64, 2980. (b) Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946.
    • (c) Donohoe, T. J. Synlett 2002, 1223.
    • (30) O'Brien, P.; Childs, A. C.; Ensor, G. J.; Hill, C. L.; Kirby, J. P.; Dearden, M. J.; Oxenford, S. J.; Rosser, C. M. Org. Lett. 2003, 5, 4955.
    • (31) Henbest, H. B.; Wilson, R. A. L. J. Chem. Soc. 1957, 1958.
    • (32) Li, Y.; Jardine, K. J.; Tan, R.; Song, D.; Dong, V. M. Angew.
    • Chem., Int. Ed. 2009, 48, 9690.
    • (33) Rohlmann, R.; Daniliuc, C.-G.; Mancheno, O. G. Chem.
    • Commun. 2013, 49, 11665.
    • (34) Parmar, N. J.; Pansuriya, B. R.; Labana, B. M.; Kant, R.; Gupta, V. K. RSC Adv. 2013, 3, 17527.
    • (35) Lee, J. I.; Lee, H. S.; Kim, B. H. Synth. Commun. 1996, 26, 3201.
    • (36) Arai, S.; Koike, Y.; Hada, H.; Nishida, A. J. Org. Chem. 2010, 75, 7573.
    • (37) Petros, A. M.; Dinges, J.; Augeri, D. J.; Baumeister, S. A.; Betebenner, D. A.; Bures, M. G.; Elmore, S. W.; Hajduk, P. J.; Joseph, M. K.; Landis, S. K.; Nettesheim, D. G.; Rosenberg, S. H.; Shen, W.; Thomas, S.; Wang, X.; Zanze, I.; Zhang, H.; Fesik, S. W. J. Med. Chem.
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