Abstract
A new convenient method for the synthesis of 1,4-benzothiazepin-5-ones by a one-pot procedure including condensation of thiosalicylic acid with chloroacetone and the reaction of the resulting 2-(acetoxythio)benzoic acid without isolation with primary amines and isocyanides is proposed. This method can be used for the combinatorial search of compounds with biological activities in the 1,4-benzothiazepine series.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R. V. A. Orru and M. de Greef, Synthesis, 2003, 1471.
L. Weber, K. Illgen, and M. Almstetter, Synlett, 1999, 366.
I. Ugi and A. Doemling, Angew. Chem., Int. Ed., 2000, 39, 3168.
M. Mironov, M. Kleban, V. Berseneva, V. Mokrushin, and V. Bakulev, Abstract Book. First Symposium of the European Society for Combinatorial Sciences, Budapest, 2001, L44.
T. Godfraind, R. Miller, and M. Wibo, Parmacol. Rev., 1986, 38, 21.
J. Slade, J. L. Stanton, D. Ben-David, and G. C. Mazzenga, J. Med. Chem., 1985, 28, 1517.
A. Nefzi, N. A. Ong, M. A. Giulianotti, J. M. Ostresh, and R. A. Houghten, Tetrahedron Lett., 1999, 40, 4939.
M. K. Schwarz, D. Tumelty, and M. A. Gallop, J. Org. Chem., 1999, 64, 2219.
N. K. Terrett, Combinatorial Chemistry, Oxford University Press, 1998, 186 p.
A. Doemling, K.-Z. Chi, and M. Barrere, Bioorg. Med. Chem. Lett., 1999, 9, 2871.
K. M. Short and A. M. M. Mjalli, Tetrahedron Lett., 1997, 38, 359; J. Zhang, A. Jacobson, J. R. Rusche, and W. Herlihy, J. Org. Chem., 1999, 64, 1074; S. Marcaccini, R. Pepino, T. Torroba, D. Miguel, and M. Garcia-Valverde, Tetrahedron Lett., 2002, 43, 8591.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Mironov, M.A., Ivantsova, M.N., Tokareva, M.I. et al. New synthesis of 1,4-benzothiazepin-5-ones. Russian Chemical Bulletin 53, 1232–1236 (2004). https://doi.org/10.1023/B:RUCB.0000042278.14695.b3
Issue Date:
DOI: https://doi.org/10.1023/B:RUCB.0000042278.14695.b3