Abstract
A method for the synthesis of 2-(1,3-diphenyl-1H-1,2,4-triazol-5-yl)-2,2-dinitroacetonitrile was developed, and its reaction with diazomethane was investigated to show the reaction involves 1,3-dipolar cycloaddition and forms a separable mixture of 4-[(1,3-diphenyl-1H-1,2,4-triazol-5-yl)dinitromethyl]-2H-1,2,3-triazoles. The latter react with KOH in ethanol to form potassium salts of 4-[(1,3-diphenyl-1H-1,2,4-triazole-5-yl)aci-nitromethyl]-1,2,3-triazoles.
Similar content being viewed by others
REFERENCES
Shevtsova, I.A. and Tyrkov, A.G., Russ. J. Org. Chem., 2007, vol. 43, p. 1742. https://doi.org/10.1134/S1070428007110309
Tyrkov, A.G. and Abdelraheem, M.A., Chem. Heterocycl. Compd., 2013, vol. 49, p. 712. https://doi.org/10.1007/s10593-013-1302-5
Terpigorev, A.N., Tselinskii, I.V., Makarevich, A.V., Frolova, G.M., and Mel’nikov, A.A., Zh. Org. Khim., 1987, vol. 23, p. 244.
Abdelrakhim, M.A., Tyrkov, A.G., and Yurtaeva, E.A., Russ. J. Org. Chem., 2014, vol. 50, p. 280. https://doi.org/10.1134/S1070428014020237
Hantzsch, A. and Rickenberger, A., Ber., 1899, vol. 32, p. 628.
Tyrkov, A.G., Candidate Sci. (Chem.) Dissertation, Leningrad, 1990.
Shlyapochnikov, V.A., Kolebatel’nye spektry alifaticheskikh nitrtosoedinenii (Vibrational Spectra of Aliphatic Nitro Compounds), Ivshin, V.P., Ed., Ioshkar-Ola: Izd. Udm. Gos. Univer., 2007.
Ladyzhnikova, T.D., Solov’ev, N.A., Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1988, vol. 24, p. 644.
Makhikova, A.V., Sukhanov, G.P., Vereshchagin, L.I., and Gareev, G.A., Izv. Vuzov, Ser. Khim. Khim, Tekhnol., 1984, vol. 27, p. 172.
Tyrkov, A.G., Solovev, N.A., Ladyzhnikova, T.D., and Altukhov, K.V., Russ. J. Org. Chem., 2004, vol. 40, p. 1151. https://doi.org/10.1023/B:RUJO.0000045897.50456.f7
Ivanov, A.I., Slovetskii, V.I., Shevelev, S.A., Erashko, V.I., Fainzil’berg, A.A., and Novikov, S.S., Zh. Fiz. Khim., 1966, vol. 40, p. 2298.
Kirkhner, Yu., Tonkosloinaya khromatografiya (Thin Layer Chromatography), Moscow: Mir, 1981, vol. 1, p. 129.
Shchurova, N.A. and Tyrkov, A.G., Zh. Org. Khim., 2006, vol. 42, p. 1592.
Obshchii praktikum po organicheskoi khimii (General Practical Works on Organic Chemistry), Kost, A.N., Ed., Moscow: Mir, 1965.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Tyrkov, A.G., Yurtaeva, E.A. Synthesis of 2-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)-2,2-dinitroacetonitrile and Its Reaction with Diazomethane. Russ J Org Chem 56, 1407–1411 (2020). https://doi.org/10.1134/S1070428020080114
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020080114