Coupling of 3-substituted 1,2,4-triazole-5-diazonium salts with ethyl acetoacetate afforded 1,2,4-triazol-5-ylhydrazones, the reaction of which with dimethylformamide dimethyl acetal leads to the formation of the corresponding readily separable 4-[2-(dimethylamino)-vinyl][1,2,4]triazolo[5,1-c][1,2,4]triazine-3-carboxylates. New pyrido[4,3-e][1,2,4]triazolo[5,1-c][1,2,4]triazin-6(7H)-ones were synthesized by the condensation of the latter with primary amines.
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(a) Gray, E. J.; Stevens, M. F. G.; Tennant, G.; Vevers, R. J. S. J. Chem. Soc., Perkin Trans. 1 1976, 1496. (b) Elnagdi, M. H.; Elmoghayar, M. R. H.; Fahmy, S. M.; Ibraheim, M. K. A.; Alnima, H. H. Z. Naturforsch. B: J. Chem. Sci. 1978, 33b, 216. (c) Farag, A. M.; Dawood, K. M.; Kandeel, Z. E. Tetrahedron 1996, 52, 7893. (d) Hassan, A. Y.; Sarg, M. T.; Bayoumi, A. H.; El-Deeb, M. A. J. Heterocycl. Chem. 2018, 55, 1450. (e) Sayed, S. M.; Raslan, M. A.; Khalil, M. A.; Dawood, K. M. Heteroat. Chem. 1999, 10, 385. (f) Hafez, E. A. A.; Abed, N. M.; Elsakka, I. A.; Elnagdi, M. H. J. Heterocycl. Chem. 1983, 20, 285. (g) Dawood, K. M.; Farag, A. M.; Abdel-Aziz, H. A. J. Chem. Res. 2005, 378. (h) Khalil, M. A.; Sayed, S. M.; Raslan, M. A. J. Chem. Soc. 2013, 57, 612. (i) Abd El Latif, F. M.; El Rady, E. A.; Khalil, M. A. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 2497. (j) Voinkov, E. K.; Ulomskiy, E. N.; Rusinov, V. L.; Chupakhin, O. N.; Gorbunov, E. B.; Drokin, R. A.; Fedotov, V. V. Chem. Heterocycl. Compd. 2015, 51, 1057. [Khim. Geterotsikl. Soedin. 2015, 51, 1057.] (k) Hamdy, N. A.; Abdel-Aziz, H. A.; Farag, A. M.; Fakhr, I. M. I. Monatsh. Chem. 2007, 138, 1001. k El Rady, E. A. Heterocycl. Commun. 2012, 18, 215. l Dawood, K. M.; Farag, A. M.; Ragab, E. A.; Kandeel, Z. E. J. Chem. Res., Synop. 2000, 206. m Gomha, S. M.; Khalil, K. D.; El-Zanaty, A. M.; Riyadh, S. M. Heterocycles 2013, 87, 1109.
Riyadh, S. M.; Kheder, N. A.; Asiry, A. M. Monatsh. Chem. 2013, 144, 1559.
Ulomskii, E. N.; Deev, S. L.; Shestakova, T. S.; Rusinov, V. L.; Chupakhin, O. N. Russ. Chem. Bull., Int. Ed. 2002, 51, 1737. [Izv. Akad. Nauk, Ser. Khim. 2002, 1594.]
Abdelhamid, A. O.; Zohdy, H. F.; Zaida, M. M. Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39B, 202.
(a) Crespan, E.; Alexandrova, L.; Khandazhinskaya, A.; Jasko, M.; Kukhanova, M.; Villani, G.; Hübscher, U.; Spadari, S.; Maga, G. Nucleic Acids Res. 2007, 35, 45. (b) Rusinov, V. L.; Ulomskii, E. N.; Chupakhin, O. N.; Zubairov, M. M.; Kapustin, A. B.; Mitin, N. I.; Zhiravetskii, M. I.; Vinograd, I. A. Pharm. Chem. J. 1990, 24, 646. [Khim. Farm. Zh. 1990, 24(9), 41.] (c) Rusinov, V. L.; Ulomskii, E. N.; Chupakhin, O. N.; Charushin, V. N. Russ. Chem. Bull., Int. Ed. 2008, 57, 985. [Izv. Akad. Nauk, Ser. Khim. 2008, 967.]
(a) Piercey, D. G.; Chavez, D. E.; Scott, B. L.; Imler, G. H.; Parrish, D. A. Angew. Chem. 2016, 128, 15541. (b) Kumar, D.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. Chem.–Eur. J. 2017, 23, 1743. (c) Wang, Q.; Shao, Y.; Lu, M. Chem. Commun. 2019, 55, 6062. (d) Anikin, O. V.; Leonov, N. E.; Klenov, M. S.; Churakov, A. M.; Voronin, A. A.; Guskov, A. A.; Muravyev, N. V.; Strelenko, Yu. A.; Fedyanin, I. V.; Tartakovsky, V. A. Eur. J. Org. Chem. 2019, 4189.
(a) Shaaban, M. R.; Saleh, T. S.; Farag, A. M. Heterocycles 2009, 78, 699. (b) Shawali, A. S.; Haboub, A. J. M. J. Chem. Res. 2011, 35, 341. (c) Raslan, M. A.; Omran, O. A. J. Heterocycl. Chem. 2016, 53, 1121. (d) Abdelhamid, A. O.; Fahmi, A. A.; Baaiu, B. S. J. Heterocycl. Chem. 2016, 53, 1917. (e) Eldebss, T. M. A.; Farag, A. M.; Shamy, A. Y. M. J. Heterocycl. Chem. 2019, 56, 371.
Abdelhamid, A. O.; Gomha, S. M.; El-Enany, W. A. M. A. J. Heterocycl. Chem. 2019, 56, 426.
(a) Vilarrasa, J.; Granados, R. J. Heterocycl. Chem. 1974, 11, 867. (b) Castillón, S.; Meléndez, E.; Vilarrasa, J. J. Heterocycl. Chem. 1982, 19, 61. (c) Chen, W.-B.; Li, Z.-X.; Yu, X.-W.; Yang, M.; Qiu, Y.-X.; Dong, W. New J. Chem. 2015, 39, 1222. (d) Sadchikova, E. V.; Mokrushin, V. S. Russ. Chem. Bull., Int. Ed. 2005, 54, 354. [Izv. Akad. Nauk, Ser. Khim. 2005, 348.]
Mawlood, M. N.; Potapov, A. Yu.; Vandyshev, D. Yu.; Shikhaliev, Kh. S.; Potapov, M. A.; Ledenyova, I. V.; Kosheleva, E. A. Chem. Heterocycl. Compd. 2019, 55, 1075. [Khim. Geterotsikl. Soedin.2019, 55, 1075.]
Magee, V. L.; Rao, C. B.; Glinka, J.; Hui, H.; Amick, T. J.; Fiscus, D.; Kakodkar, S.; Nair, M.; Shechter, H. J. Org. Chem. 1987, 52, 5538.
Barsy, M. A. J. Chin. Chem. Soc. 2003, 50, 1189.
Tennant, G.; Vevers, R. J. S. J. Chem. Soc., Perkin Trans. 1 1976, 421.
(a) Shikhaliev, Kh. S.; Potapov, A. Yu.; Poluchin, E. L.; Slivkin, A. I. Russ. Chem. Bull., Int. Ed. 2009, 58, 1996. [Izv. Akad. Nauk, Ser. Khim. 2009, 1934.] (b) Didenko, V. V.; Potapov, A. Yu.; Ledenyova, I. V.; Shikhaliev, Kh. S.; Konushko, O. V. Russ. J. Gen. Chem. 2010, 80, 814. [Zh. Obshch. Khim. 2010, 80, 653.]
The study was supported by a grant from the Russian Science Foundation (project no. 18-74-10097).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1348–1352
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Mawlood, M.N., Potapov, M.A., Ledenyova, I.V. et al. Synthesis of new pyrido[4,3-e][1,2,4]triazolo-[5,1-c][1,2,4]triazin-6(7H)-ones. Chem Heterocycl Comp 56, 1348–1352 (2020). https://doi.org/10.1007/s10593-020-02821-2
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DOI: https://doi.org/10.1007/s10593-020-02821-2