Abstract
By six examples, it was demonstrated that nitrosylsulfuric acid can be successfully used for oxidation of 3,5-diaryl-4,5-dihydroisoxazoles to the corresponding 3,5-diarylisoxazoles. If the starting isoxazolines contain the aromatic substituents activated towards electrophilic substitution, nitration of both newly formed isoxazole and substituted benzene rings occurred.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
B. P. Kansagra, H. H. Bhatt, A. R. Parikh, Indian J. Heterocycl. Chem., 2002, 12, 61.
S. G. Kini, A. R. Bhat, R. Bhat, N. Narayanaswamy, Indian J. Heterocycl. Chem., 2008, 17, 319.
V. S. Parmar, N. K. Sharma, M. Husain, A. C. Watterson, J. Kumar, L. A. Samuelson, A. L. Cholli, A. K. Prasad, A. Kumar, S. Malhotra, N. Kumar, A. Jha, A. Singh, I. Singh, Himanshu, A. Vats, N. A. Shakil, S. Trikha, S. Mukherjee, S. K. Sharma, S. K. Singh, A. Kumar, H. N. Jha, C. E. Olsen, C. P. Stove, M. E. Bracke, M. M. Mareel, Bioorg. Med. Chem., 2003, 11, 913.
A. Kumar, S. Rout, C. S. Panda, M. B. V. Raju, B. V. V. Ravikumar, J. Adv. Pharm. Res., 2011, 2, 94.
L. Babar, S. S. Tomar, Pestic. Res. J., 2005, 17. No. 2, 1.
A. Upadhyay, M. Gopal, C. Srivastava, N. D. Pandey, J. Pestic. Sci. (Tokyo, Jpn.), 2010, 35, 464.
D. A. Patrick, S. A. Bakunov, S. M. Bakunova, E. V. K. Suresh Kumar, R. J. Lombardy, S. K. Jones, A. S. Bridges, O. Zhirnov, J. E. Hall, T. Wenzler, R. Brun, R. R. Tidwill, J. Med. Chem., 2007, 50, 2468.
Pat. WO 2000008001 A1; http://patentscope.wipo.int.
T. Haddad, R. Gershman, R. Dilis, D. Labaree, R. B. Hochberg, R. N. Hanson, Bioorg. Med. Chem. Lett., 2012, 22, 5999.
A. A. Vieira, F. R. Bryk, G. Conte, A. J. Bortoluzzi, H. Gallardo, Tetrahedron Lett., 2009, 50, 905.
G. D. Vilela, R. R. da Rosa, P. H. Schneider, I. H. Bechtold, J. Eccher, A. A. Merlo, Tetrahedron Lett., 2011, 52, 6569.
A. Khatyr, H. Maas, G. Calzaferri, J. Org. Chem., 2002, 67, 6705.
M. Tanaka, T. Haino, K. Ideta, K. Kubo, A. Mori, Y. Fukazawa, Tetrahedron, 2007, 63, 652.
A. M. Jawalekar, E. Reubsaet, F. P. J. T. Rutjes, F. L. van Delft, Chem. Commun., 2011, 47, 3198.
K. V. G. C. Sekhar, T. V. N. V. T. Sasank, H. N. Nagesh, N. Suresh, K. M. Naidu, A. Suresh, Chin. Chem. Lett., 2013, 24, 1045.
S. Tang, J. He, Y. Sun, L. He, X. She, Org. Lett., 2009, 11, 3982.
C. J. Easton, C. M. Hughes, E. R. T. Tiekink, C. E. Lubin, G. P. Savage, G. W. Simpson, Tetrahedron Lett., 1994, 35, 3589.
C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, Adv. Heterocycl. Chem., 1994, 60, 261.
V. G. Desai, S. G. Tilve, Synth. Commun., 1999, 29, 3017.
A. Barco, S. Bennetti, G. P. Pollini, P. G. Baraldi, Synthesis, 1977, 837.
M. V. Gorelik, B. L. Lomzakova, Zh. Org. Khim. [Russ. J. Org. Chem.], 1978, 14, 1051 (in Russian).
U. Türck, H. Behringer, Chem. Ber., 1965, 98, 3020.
O. Dann, H. Fick, B. Pietzner, E. Walkenhorst, R. Fernbach, D. Zeh, Liebigs Ann. Chem., 1975, 160.
H.-K. Fun, S. Arshad, S. Samshuddin, B. Narayana, B. K. Sarojini, Acta Crystallogr., Sect. E: Struct. Rep. Online, 2012, 68. o1783.
D. R. Chrisope, R. A. Keel, A. L. Baumstark, D. W. Boykin, J. Heterocycl. Chem., 1981, 18, 795.
J.-P. Hauff, J. Tuaillon, R. Perrot, Helv. Chim. Acta, 1978, 61, 1207
A. D. Kadzhaeva, E. V. Trofimova, R. A. Gazzaeva, A. N. Fedotov, S. S. Mochalov, Moscow Univ. Chem. Bull., 2009, 64, 28.
L. G. Saginova, M. Al-Hamdan, V. S. Petrosyan, Vestn. MGU, Ser. 2. Khimiya [Moscow Univ. Chem. Bull.], 1999, 40, 46 (in Russian).
Praktikum po neorganicheskoikhimii: Uchebnoe posobie dlya studentov vysshikh uchebnykh zavedenii[Laboratory Course ofInorganic Chemistry: A Textbook for Students ofHigher Educa tional Institutions], Ed. Yu. D. Tret´yakov, Akademiya, Moscow, 2004, p. 241 (in Russian).
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0517—0520, March, 2018.
Rights and permissions
About this article
Cite this article
Bondarenko, O.B., Komarov, A.I., Kuznetsova, L.I. et al. Nitrosylsulfuric acid as an oxidant in the synthesis of 3,5-diarylisoxazoles. Russ Chem Bull 67, 517–520 (2018). https://doi.org/10.1007/s11172-018-2103-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2103-x