Abstract
1,6-Dihydro-1,6-dihydroxybenzo[1,2-d:3,4-d′]bistriazole and 4- and 5-nitro-1,6-dihydro-1,6-dihydroxybenzo[1,2-d:3,4-d′]bistriazole were synthesized starting from 2,4-dinitrosore-sorcinol, whereas 4,7-dihydro-1,4,7-trihydroxy-1H-benzo[1,2-d:3,4-d′:5,6-d″]tris[1,2,3]-triazole was synthesized starting from phloroglucinol. The reaction of trinitrosophloroglucinol with hydrazine hydrate in acetic acid led to 2,4,6-tridiazocyclohexane-1,3,5-trione.
Similar content being viewed by others
References
A. A. Berlin, F. A. Shutov, Khimiya i tekhnologiya gazonapolnennykh vysokopolimerov [Chemistry and Technology of Higher Polymers Filled with Gas], Nauka, Moscow, 1980, 503 pp. (in Russian).
Fr. Pat. 1387191; Chem. Abstrs, 1965, 62, 12002.
A. I. Busev, Sintezy novykh organicheskikh reagentov dlya neorganicheskogo analiza [Synthesis of New Organic Reagents for Inorganic Analysis], MGU Publ., Moscow, 1972, 198 pp. (in Russian).
E. Yu. Belyaev, B. V. Gidaspov, Aromaticheskie nitrozosoedineniya [Aromatic Nitroso Compounds], Khimiya, Leningrad, 1989, 175 pp. (in Russian).
W. Borsche, H. Weber, J. Liebigs Ann. Chem., 1931, 489, 270.
E. Buncel, J. Dust, Can. J. Chem., 1988, 66, 1712.
J. Dust, E. Buncel, Can. J. Chem., 1991, 69, 978.
V. A. Samsonov, L. B. Volodarskii, V. L. Korolev, G. Kh. Khisamutdinov, Khim. Geterotsikl. Soedin., 1993, 1364 [Chem. Heterocycl. Compd. (Engl.Transl.), 1993, 29, 1169].
V. A. Samsonov, G. E. Sal’nikov, A. M. Genaev, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 2369 [Izv. Akad. Nauk, Ser. Khim., 2009, 2294].
R. Bosch, G. Jung, W. Winter, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1983, 39, 1089.
O. L. Brady, C. V. Reynold, J. Chem. Soc., 1928, 193.
Cambridge Structural Database, Version 5.31 (Updates August 2010), University of Cambridge, Cambridge, UK.
R. A. Renfrow, M. J. Strauss, S. Cohen, E. Buncel, Aust. J. Chem., 1983, 36, 1843.
H.-L. Wen, Y.-H. Chen, H.-W. Hu, X.-Y. Zhou, C.-B. Liu, Acta Crystallogr., 2006, E62, o4702.
I. V. Ovchinnikov, M. A. Epishina, S. I. Molotov, Y. A. Strelenko, K. A. Lyssenko, N. N. Makhova, Mendeleev Commun., 2003, 272.
R. Benedikt, Ber. Deutsch. Chem. Ges., 1878, 11, 1374.
K. Frandenberg, H. Fikentscher, W. Wenter, Justus Liebigs Ann. Chem., 1925, 442, 309.
B. Kohne, K. Praefcke, T. Derz, T. Gondro, F. Frolow, Angew. Chem., Int. Ed., 1986, 25, 650.
L. R. Sutton, W. A. Donaubauer, F. Hampel, A. Hirsch, Chem. Commun., 2004, 1758.
W. Ried, H. Mengler, Fortschr. Chem. Forsch., 1965, 5/1, 15.
G. Casini, F. Gualtieri, M. L. Stein, Gazz. Chim. Ital., 1965, 95, 983.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1760–1766, September, 2012.
Rights and permissions
About this article
Cite this article
Samsonov, V.A., Gatilov, Y.V. & Volodarskii, L.B. Synthesis of 1,6-dihydro-1,6-dihydroxybenzo[1,2-d:3,4-d′]bistriazole, 4- and 5-nitro-1,6-dihydro-1,6-dihydroxybenzo[1,2-d:3,4-d′]bistriazole and 4,7-dihydro-1,4,7-trihydroxy-1H-benzo-[1,2-d:3,4-d′:5,6-d″]tris[1,2,3]triazole. Russ Chem Bull 61, 1776–1782 (2012). https://doi.org/10.1007/s11172-012-0244-x
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0244-x