Abstract
Nucleophilic substitution of the nitro group in a model representative of N-aminopyrazoles, 1-amino-3,4-dinitropyrazole, has been studied for the first time. The compound was shown to undergo nucleophilic substitution with S-nucleophiles. The reaction was effected with regioselective substitution of the nitro group at position 3 and in good yields.
This is a preview of subscription content, log in via an institution to check access.
References
L. Dalinger, I. A. Vatsadze, T. K. Shkineva, G. P. Popova, S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2012, 461 [Russ. Chem. Bull., Int. Ed., 2011, 60, 464].
V. V. Kuzmenko, A. F. Pozharskii, Adv. Heterocyclic Chem., 1993, 53, 85
V. M. Vinogradov, I. L. Dalinger, S. A. Shevelev, Khim. Farm. Zh., 1994, 37 [Pharm. Chem. J. (Engl. Transl.), 1994]
M. I. Rodriguez-Franco, I. Dorronsoro, A. Martinez, C. Perez, A. Badia, Arch. Pharm., 2000, 333, 118
WO 2004069196 A2 20040819, 2004.
V. M. Vinogradov, I. L. Dalinger, S. A. Shevelev, Mendeleev Commun., 1993, 111
V. M. Vinogradov, I. L. Dalinger, V. I. Gulevskaya, S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 1993, 1434 [Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 1369].
I. L. Dalinger, T. I. Cherkasova, S. A. Shevelev, Mendeleev. Commun., 1997, 58
A. A. Zaitsev, I. L. Dalinger, A. M. Starosotnikov, V. V. Kachala, Yu. A. Strelenko, T. K. Shkineva, S. A. Shevelev, Zh. Org. Khim., 2005, 41, 1538 [Russ. J. Org. Chem. (Engl. Transl.), 2005, 41, 1507]
A. A. Zaitsev, T. I. Cherkasova, I. L. Dalinger, V. V. Kachala, Yu. A. Strelenko, T. K. Shkineva, I. V. Fedyanin, V. N. Solkan, G. P. Popova, S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2007, 2004 [Russ. Chem. Bull., Int. Ed., 2007, 56, 2074]
I. L. Dalinger, T. I. Cherkasova, G. P. Popova, T. K. Shkineva, I. A. Vatsadze, S. A. Shevelev, M. I. Kanishchev, Izv. Akad. Nauk, Ser. Khim., 2009, 404 [Russ. Chem. Bull., Int. Ed., 2009, 58, 410]
A. A. Zaitsev, I. O. Kortusov, I. L. Dalinger, V. V. Kachala, G. P. Popova, S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2009, 2054 [Russ. Chem. Bull., Int. Ed., 2009, 58, 2118]
A. A. Zaitsev, D. V. Zaiko, I. L. Dalinger, V. V. Kachala, T. K. Shkineva, S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2009, 2058 [Russ. Chem. Bull., Int. Ed., 2009, 58, 2122].
I. L. Dalinger, I. A. Vatsadze, T. K. Shkineva, I. O. Kortusov, G. P. Popova, V. V. Kachala, S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2010, 1739 [Russ. Chem. Bull., Int. Ed., 2010, 59, 1786].
L. Larina, V. Lopyrev, Nitroazoles. Synthesis, Structure and Applications, Springer, LLC, 2009, 196.
Author information
Authors and Affiliations
Corresponding author
Additional information
For Part 20, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 464–465, February, 2012.
Rights and permissions
About this article
Cite this article
Shkineva, T.K., Dalinger, I.L., Vatsadze, I.A. et al. Nitropyrazoles 21. Selective nucleophilic substitution of the nitro group in 1-amino-3,4-dinitropyrazole. Russ Chem Bull 61, 467–468 (2012). https://doi.org/10.1007/s11172-012-0066-x
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0066-x