Abstract
Tetrazolo[1,5-a][1,4]benzodiazepines were obtained by an efficient azide five-centered four-component Ugi reaction, which used ketones, sodium azide, ammonium chloride, and the corresponding isonitrile. Scope and limitations of this multi-component reaction were considered.
Similar content being viewed by others
References
C. I. Neutel, J. P. Hirdes, C. J. Maxwell, S. B. Patten, Age Ageing, 1996, 25, 273.
S. Fotso, Mini-Reviews in Organic Chemistry, 2010, 7, 68—74
L. Loudni, J. Roche, V. Potiron, J. Clarhaut, C. Bachmann, J. P. Gesson, I. Tranoy-Opalinski, Bioorg. Med. Chem. Lett., 2007, 17, 4819.
M. Schwarz, L. Turski, W. Janiszewski, K. H. Sontag, Neuroscience Lett., 1983, 36, 175–180
M. Kita, D. E. Goodkin, Drugs, 2000, 59, 487.
N. S. Cho, K. Y. Song, C. Pa’rka’nyi, J. Heterocycl. Chem., 1989, 26, 1807.
F. M. Rivas, J. P. Stables, L. Murphree, R. V. Edwankar, C. R. Edwankar, S. Huang, H. D. Jain, Y. Zhou, S. Majumder, S. Sankar, B. L. Roth, J. Ramerstorfer, R. Furtmüller, W. Sieghart, J. M. Cook, J. Med. Chem., 2009, 52, 1795.
J. Spencer, R. P. Rathnam, A. L. Harvey, C. J. Clements, R. L. Clark, M. P. Barrett, P. E. Wong, L. Male, S. J. Coles, S. P. Mackay, Bioorg. Med. Chem., 2011, 19, 1802.
K. K. Vijaya Raj, B. Narayana, N. Suchetha Kumari, B. V. Ashalatha, B. K. Sarojini, J. Pharmacol. Toxicol., 2006, 1, 471.
E. K. Killam, A. Suria, Benzodiazepines, in Antiepileptic Drugs: Mechanisms of Action; Advances in Neurology; Eds G. H. Glaser, J. K. Penry, D. M. Woodbury, Raven Press, New York, 1980, 27, 597—615
R. L. MacDonald, Benzodiazepines: Mechanisms of Action, in Antiepileptic Drugs, 5th ed., Eds R. H. Levy, R. H. Mattson, B. S. Meldrum, E. Perucca, Lippincott Williams and Wilkins, Philadelphia, 2002, 179–186.
U.S. Pat. 5,705,890, 1998.
Eur. Pat. 0523846, 1993.
I. Ugi, C. Steinbruckner, Chem. Ber., 1961, 94, 734
I. Ugi, Angew. Chem., Int. Ed. Engl., 1962, 1, 8.
R. S. Borisov, A. I. Polyakov, L. A. Medvedeva, V. N. Khrustalev, N. I. Guranova, L. G. Voskressensky, Org. Lett., 2010, 12, 3894.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1592—1598, August, 2012.
Rights and permissions
About this article
Cite this article
Borisov, R.S., Polyakov, A.I., Medvedeva, L.A. et al. Synthesis of tetrazolodiazepines by a five-centered four-component azide Ugi reaction. Scope and limitations. Russ Chem Bull 61, 1609–1615 (2012). https://doi.org/10.1007/s11172-012-0214-3
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0214-3