Benzonitrile Oxide Cycloadditions with Exocyclic Methylene Benzothiazepine Dioxides
Sarah J. Ryan A , Craig L. Francis A and G. Paul Savage A B
+ Author Affiliations
- Author Affiliations
A CSIRO Materials Science and Engineering, Private Bag 10, Clayton South MDC, Vic. 3169, Australia.
B Corresponding author. Email: paul.savage@csiro.au
Australian Journal of Chemistry 67(3) 381-388 https://doi.org/10.1071/CH13444
Submitted: 26 August 2013 Accepted: 23 September 2013 Published: 14 October 2013
Abstract
N-substituted 5-methylene-2,3,4,5-tetrahydrobenzo[f][1,2]thiazepine 1,1-dioxides underwent 1,3-dipolar cycloaddition with benzonitrile oxide, generated in situ, to give isoxazoline spiro adducts. The cycloadditions were completely regioselective to give the hitherto unreported 3,4-dihydro-2H,4′H-spiro[benzo[f][1,2]thiazepine-5,5′-isoxazole] 1,1-dioxide cycloadduct. Where the N-substituent on the sulfonamide cycloaddition precursor was a 2-substituted arene, the resulting atropisomerism along the N-aryl bond led to facial selectivity in the cycloaddition reaction, with greater than 90 % diastereoselectivity.
References
[1] T. S. Peat, D. I. Rhodes, N. Vandegraaff, G. Le, J. A. Smith, L. J. Clark, E. D. Jones, J. A. V. Coates, N. Thienthong, J. Newman, O. Dolezal, R. Mulder, J. H. Ryan, G. P. Savage, C. L. Francis, J. J. Deadman, PLoS ONE 2012, 7, e40147.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVGmtrfI&md5=f5671c1f8aa85b4ace9448633bc09851CAS | 22808106PubMed |
[2] D. I. Rhodes, T. S. Peat, N. Vandegraaff, D. Jeevarajah, G. Le, E. D. Jones, J. A. Smith, J. A. V. Coates, L. J. Winfield, N. Thienthong, J. Newman, D. Lucent, J. H. Ryan, G. P. Savage, C. L. Francis, J. J. Deadman, Antivir. Chem. Chemother. 2011, 21, 155.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXivF2mtLc%3D&md5=9fe6bef6d64f384ed3d8313c4c99f2f8CAS | 21602613PubMed |
[3] J. Clardy, C. Walsh, Nature 2004, 432, 829.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVOht7jP&md5=b6a14ec4a09ce807ae44e2ecf94951a6CAS | 15602548PubMed |
[4] A. D. Morley, A. Pugliese, K. Birchall, J. Bower, P. Brennan, N. Brown, T. Chapman, M. Drysdale, I. H. Gilbert, S. Hoelder, A. Jordan, S. V. Ley, A. Merritt, D. Miller, M. E. Swarbrick, P. G. Wyatt, Drug Discov. Today 2013, in press.
| Crossref | GoogleScholarGoogle Scholar | 23906694PubMed |
[5] F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 2009, 52, 6752.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1KjtLvN&md5=1be92b1310beca07aef8d83f3d16b003CAS | 19827778PubMed |
[6] P. D. Leeson, S. A. St-Gallay, M. C. Wenlock, Med. Chem. Commun. 2011, 2, 91.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1yktbo%3D&md5=384e7ba0354711cbd061a4b1c14006beCAS |
[7] T. J. Ritchie, S. J. F. Macdonald, R. J. Young, S. D. Pickett, Drug Discov. Today 2011, 16, 164.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhvVyqsr0%3D&md5=fa6d21c3a271681b88029b788714c3c4CAS | 21129497PubMed |
[8] W. H. B. Sauer, M. K. Schwarz, J. Chem. Inf. Comput. Sci. 2003, 43, 987.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhvF2muro%3D&md5=2385f00ef0f956ecdd3cd882a4b3d1e4CAS |
[9] P. Grunanger, P. Vita-Finzi, Isoxazoles – Part 1 (Eds A. Weissberger, E. C. Taylor) The Chemistry of Heterocyclic Compounds 1991, Vol. 49 (Wiley: New York, NY).
[10] C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, in Cycloaddition Reactions of Nitrile Oxides with Alkenes (Ed. A. R. Katritzky) 1994, Vol. 60, pp. 261–327 (Academic Press: San Diego, CA.).
[11] S. M. Pereira, G. P. Savage, G. W. Simpson, R. J. Greenwood, M. F. Mackay, Aust. J. Chem. 1993, 46, 1401.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXitFOgtbY%3D&md5=dcc40d60ce1f63e7cc526d47b99f1c6eCAS |
[12] B. M. Kelly-Basetti, M. F. Mackay, S. M. Pereira, G. P. Savage, G. W. Simpson, Heterocycles 1994, 37, 529.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXkvVeqsro%3D&md5=325f780c35a79819f70c0ec62c9d0e0bCAS |
[13] C. K. Y. Lee, C. J. Easton, G. P. Savage, G. W. Simpson, ARKIVOC 2006, 3, 175.
[14] R. Newton, G. P. Savage, Aust. J. Chem. 2008, 61, 432.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXntlGjs70%3D&md5=c8907dfe7b054d50a70658304f4f8f39CAS |
[15] N. J. Beattie, C. L. Francis, A. J. Liepa, G. P. Savage, Aust. J. Chem. 2010, 63, 445.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjvV2rsbg%3D&md5=e88a5ccf05f27e437c0f09b4f65d5f87CAS |
[16] A. M. Said, G. P. Savage, J. Org. Chem. 2011, 76, 6946.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXptFKnu7k%3D&md5=a31df04f9cce97a372c3c6c2c5918f24CAS | 21739981PubMed |
[17] S. L. Harding, G. P. Savage, Org. Biomol. Chem. 2012, 10, 4759.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XnvVSrt7o%3D&md5=105e8a89dac05a718933858e7656f1eaCAS | 22588428PubMed |
[18] G. P. Savage, Curr. Org. Chem. 2010, 14, 1478.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlCqur3L&md5=731af997b925ac6dc5f7f19a8d30e6faCAS |
[19] J. Xu, A. T. Hamme, Synlett 2008, 919.
| Crossref | GoogleScholarGoogle Scholar |
[20] S. Dadiboyena, J. Xu, A. T. Hamme, Tetrahedron Lett. 2007, 48, 1295.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotFaitg%3D%3D&md5=1ab5cc474dc6e0872760b2379defc1ddCAS | 18265873PubMed |
[21] G. P. Savage, G. T. Wernert, Aust. J. Chem. 2005, 58, 877.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlejsL3J&md5=285b73df5f09c8205e3c788c2be476cfCAS |
[22] C. J. Easton, C. M. M. Hughes, E. R. T. Tiekink, C. E. Lubin, G. P. Savage, G. W. Simpson, Tetrahedron Lett. 1994, 35, 3589.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXkvVeisbo%3D&md5=140688e6b8a77cc4598893c6647711ffCAS |
[23] S. J. Barrow, C. J. Easton, G. P. Savage, G. W. Simpson, Tetrahedron Lett. 1997, 38, 2175.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXitFKks7w%3D&md5=84916564a3c63ad6905b322f1db4fc21CAS |
[24] W.-C. Cheng, Y. Liu, M. Wong, M. M. Olmstead, K. S. Lam, M. J. Kurth, J. Org. Chem. 2002, 67, 5673.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XltV2msbc%3D&md5=247d264d032e8e9269c4df2da8bdde18CAS | 12153267PubMed |
[25] K. G. Guggenheim, J. D. Butler, P. P. Painter, B. A. Lorsbach, D. J. Tantillo, M. J. Kurth, J. Org. Chem. 2011, 76, 5803.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXnvFahurw%3D&md5=b72e14529b2358290ea41ef6780bdadcCAS | 21650164PubMed |
[26] B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Freidinger, W. L. Whitter, G. F. Lundell, D. F. Veber, P. S. Anderson, J. Med. Chem. 1988, 31, 2235.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXmtVCgurs%3D&md5=2a59a477352c66f87e29ff3aa44a418fCAS | 2848124PubMed |
[27] M. Altamura, V. Fedi, D. Giannotti, P. Paoli, P. Rossi, New J. Chem. 2009, 33, 2219.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlWks73I&md5=22b345693eb50e7faf73eb8e5dd9adefCAS |
[28] M. Wainwright, J. E. Kristiansen, Dyes Pigments 2011, 88, 231.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1KqtLfF&md5=e6070b8715c66923f7edc6f38d7c2dd1CAS |
[29] D. B. A. de Bont, K. M. Sliedregt-Bol, L. J. F. Hofmeyer, R. M. J. Liskamp, Bioorg. Med. Chem. 1999, 7, 1043.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXktFChs7k%3D&md5=0e63021d38c5bfdd92a5866806213d50CAS |
[30] A. K. Ganguly, S. S. Alluri, D. Caroccia, D. Biswas, C.-H. Wang, E. Kang, Y. Zhang, A. T. McPhail, S. S. Carroll, C. Burlein, V. Munshi, P. Orth, C. Strickland, J. Med. Chem. 2011, 54, 7176.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXht1Wks7zE&md5=4dfce8eada39f7cfda26039e82eba372CAS | 21916489PubMed |
[31] M. B. Tollefson, S. A. Kolodziej, T. R. Fletcher, W. F. Vernier, J. A. Beaudry, B. T. Keller, D. B. Reitz, Bioorg. Med. Chem. Lett. 2003, 13, 3727.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnvFGjurc%3D&md5=e98fb748123f759767208113765e7679CAS | 14552767PubMed |
[32] G. Laconde, P. Depreux, P. Berthelot, N. Pommery, J.-P. Hénichart, Eur. J. Med. Chem. 2005, 40, 167.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1Cqu7s%3D&md5=e9f8f806a44ea17a4a69c1c386dfba31CAS | 15694651PubMed |
[33] N. Lebegue, S. Gallet, N. Flouquet, P. Carato, B. Pfeiffer, P. Renard, S. Léonce, A. Pierré, P. Chavatte, P. Berthelot, J. Med. Chem. 2005, 48, 7363.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFCltbzO&md5=551c50e951a059390cc1c2784989bee0CAS | 16279796PubMed |
[34] R. Silvestri, G. Marfè, M. Artico, G. La Regina, A. Lavecchia, E. Novellino, M. Morgante, C. Di Stefano, G. Catalano, G. Filomeni, E. Abruzzese, M. R. Ciriolo, M. A. Russo, S. Amadori, R. Cirilli, F. La Torre, P. Sinibaldi Salimei, J. Med. Chem. 2006, 49, 5840.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XnvVaksbo%3D&md5=07ed6448155dbcf3089434b3a34e987dCAS | 16970408PubMed |
[35] P. Pacher, E. Kohegyi, V. Kecskemeti, S. Furst, Curr. Med. Chem. 2001, 8, 89.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhtVSgtrw%3D&md5=adc777f1467bf83fb695e664c5a32f39CAS | 11172668PubMed |
[36] D. K. Rayabarapu, A. Zhou, K. O. Jeon, T. Samarakoon, A. Rolfe, H. Siddiqui, P. R. Hanson, Tetrahedron 2009, 65, 3180.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjs1agsL0%3D&md5=3303b536044b92250a2f8e80251b7cd2CAS | 20161276PubMed |
[37] S. J. Ryan, C. L. Francis, G. P. Savage, Aust. J. Chem. 2013, 66, 874.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1Ois7zP&md5=1d1197ee4294390fbe93138d12eb0125CAS |
[38] Y. Ohta, H. Chiba, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 2009, 74, 7052.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpslaiu78%3D&md5=587a04d8c96e2099a0c967e25ec23c68CAS | 19673483PubMed |
[39] K. Ackermann, J. Chapuis, D. E. Horning, G. Lacasse, J. M. Muchowski, Can. J. Chem. 1969, 47, 4327.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3cXht1Gnsw%3D%3D&md5=fc844454e9910bff47cf86db7b5812efCAS |
[40] N. Platzer, J. P. Bouchet, C. Malen, C. Labrid, E. Mocaer, Magn. Reson. Chem. 1992, 30, 1212.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXntlWntg%3D%3D&md5=12bb3eaf528082c7a3230cf0f81043a4CAS |
[41] M. Raban, E. H. Carlson, J. Szmuszkovicz, G. Slomp, C. G. Chidester, D. J. Duchamp, Tetrahedron Lett. 1975, 16, 139.
| Crossref | GoogleScholarGoogle Scholar |
[42] M. Sarrazin, M. Bourdeaux-Pontier, C. Briand, E.-J. Vincent, Org. Magn. Resonance 1975, 7, 89.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXltFems7w%3D&md5=9611d84da107cc3fa55c0133b02060aaCAS |
[43] R. Benassi, P. Lazzeretti, F. Taddei, D. Nardi, A. Tajana, Org. Magn. Resonance 1976, 8, 387.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2sXktlSjsg%3D%3D&md5=fc14360cb1844b0ee3167f9e89a5a0e4CAS |
[44] A. Entrena, J. M. Campos, M. A. Gallo, A. Espinosa, ARKIVOC 2005, 2005, 88.
| Crossref | GoogleScholarGoogle Scholar |
[45] N. H. Martin, J. D. Brown, K. H. Nance, H. F. Schaefer, P. R. Schleyer, Z.-X. Wang, H. L. Woodcock, Org. Lett. 2001, 3, 3823.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXnvVGnu7Y%3D&md5=5fb7087effdc0a01fadf64ef3915f3ddCAS | 11720545PubMed |
[46] T. Mukaiyama, T. Hoshino, J. Am. Chem. Soc. 1960, 82, 5339.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXpvFSiug%3D%3D&md5=3cd0d3c8010da97e7b7d93b3b7635936CAS |
[47] H. Feuer, K. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis: Novel Strategies in Synthesis 2008 (John Wiley and Sons: Hoboken, NJ).
[48] G. A. Lee, Synthesis 1982, 508.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XkvFaitbc%3D&md5=0050181d5cf18a2ba99e78c33f835c06CAS |
[49] R. Sustmann, Pure Appl. Chem. 1974, 40, 569.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXls1ehtL0%3D&md5=7fa47001417180045032afe7ec16f207CAS |
[50] R. Huisgen, Angew. Chem. Int. Ed. 1963, 2, 633.
| Crossref | GoogleScholarGoogle Scholar |
