The present microreview elucidates contemporary methods for the preparation of 1,3-propanesultams (1λ6-isothiazolidine-1,1-diones) based on various types of organic reactions, namely, intramolecular condensation, sulfonylation, alkylation, as well as reduction and oxidation.
Similar content being viewed by others
References
Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2015, 137, 5638.
Spaltenstein, A.; Almond, M. R.; Bock, W. J.; Cleary, D. G.; Furfine, E. S.; Hazen, R. J.; Kazmierski, W. M.; Salituro, F. G.; Tung, R. D.; Wright, L. R. Bioorg. Med. Chem. Lett. 2000, 11, 1159.
Cherney, R. J.; Mo, R.; Meyer, D. T.; Hardman, K. D.; Liu, R. Q.; Covington, M. B.; Qian, M.; Asserman, Z. R.; Christ, D. D.; Trzaskos, J. M.; Newton, R. C.; Decicco, C. P. J. Med. Chem. 2004, 47, 2981.
Binder, D. EP Patent 0213295 A1.
Abou-Gharbia, M. A.; Schiehser, G. A.; Childress, S. J. US Patent 4732984 A.
Gymer, G. E.; Narayanaswami, S.; Richardson, K. EP Patent 0352946 A1.
Anderson, D. J.; Hester, J. B., Jr. WO Patent 2001032657 A1.
Carty, T. J.; Marfat, A.; Moore, P. F.; Falkner, F. C.; Twomey, T. M.; Weissman, A. Agents Actions 1993, 39, 157.
Hansen, J. M.; Kristensen, M.; Skovsted, L. Epilepsia 1968, 9, 17.
Brozozowski, F.; Saczewski, F.; Neamati, N. Bioorg. Med. Chem. Lett. 2006, 16, 5298.
Asinger, F.; Ebeneder, F. DE Patent 740814 C.
Lipina, E. S.; Bodina, R. I.; Efimova, T. P.; Novikova, T. A.; Perekalin, V. V. Pharm. Chem. J. 1999, 33, 598.
Hanaya, K.; Yoshioka, S.; Ariyasu, S.; Aoki, S.; Shoji, M.; Sugai, T. Bioorg. Med. Chem. Lett. 2016, 26, 545.
Enders, D.; Moll, A.; Bats J. W. Eur. J. Org. Chem. 2006, 5, 1271.
Rassadin, V. A.; Grosheva, D. S.; Arefeva, I. A.; Tomashevskiy, A. A.; Sokolov, V. V.; de Meijere, A. Eur. J. Org. Chem. 2012, 26, 5028.
Lad, N.; Sharma, R.; Marquez, V. E.; Mascarenhas, M. Tetrahedron Lett. 2013, 54, 6307.
Cleator, E.; Sheen, F. J.; Bio, M. M.; Jos Brands, K. M.; Davies, A. J.; Dolling, U.-H. Tetrahedron Lett. 2006, 47, 4245.
Preston, A. J.; Gallucci, J. C.; Paquette, L. A. J. Org. Chem. 2006, 71, 6573.
Valente, C.; Guedes, R. C.; Moreira, R.; Iley, J.; Gut, J.; Rosenthal P. J. Bioorg. Med. Chem. Lett. 2006, 16, 4115.
Song, B.; Yu, C.-B.; Huang, W.-X.; Chen, M.-W.; Zhou, Y.-G. Org. Lett. 2015, 17, 190.
Yu, C.-B.; Wang, D.-W.; Zhou, Y.-G. J. Org. Chem. 2009, 74, 5633.
Wang, Y.-Q.; Lu, S.-M.; Zhou, Y.-G. J. Org. Chem. 2007, 72, 3729.
Freitag, D.; Metz, P. Tetrahedron 2006, 62, 1799.
Matsuyama, H.; Izuoka, A.; Kobayashi, M. Heterocycles 1985, 23, 1897.
Evans, B. J.; Doi, J. T.; Musker, W. K. J. Org. Chem. 1990, 55, 2580.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 492–494
Rights and permissions
About this article
Cite this article
Popova, M.V., Dobrydnev, A.V. Synthetic approaches to 1,3-propanesultams (microreview). Chem Heterocycl Comp 53, 492–494 (2017). https://doi.org/10.1007/s10593-017-2080-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-017-2080-2