The structural characteristics of 5-aryl-3-(arylhydrazono)furan-2(3Н)-ones accessed via azocoupling of furan-2(3Н)-ones with aryldiazonium salts were established by NMR spectroscopy (including two-dimensional NMR experiments 1H–13C HMQC, 1H–15N HMQC, 1H–13C HMBC, NOE) and X-ray structural analysis techniques. The reaction of synthesized compounds with hydrazine leading to the formation of six-membered heterocycles, hydrazono-substituted 4,5-dihydropyridazin-3(2Н)-ones, was studied.
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(a) Elnagdi, M. H.; Sallam, M. M. M.; Ilias, M. A. M. Helv. Chim. Acta 1975, 58, 1944. (b) Karcı, F.; Sener, N.; Yamac, M.; Sener, I.; Demircalı, A. Dyes Pigm. 2009, 80, 47. (c) Krystof, V.; Cankar, P.; Frysova, I.; Slouka, J.; Kontopidis, G.; Dzubak, P.; Hajduch, M.; Srovnal, J.; de Azevedo, W. F., Jr.; Orsag, M.; Paprskarova, M.; Rolcık, J.; Latr, A.; Fischer, P. M.; Strnad M. J. Med. Chem. 2006, 49, 6500.
(а) Bakulev, V. A.; Berseneva, V. S.; Belskaia, N. P.; Morzherin, Y.Y.; Zaitsev, A.; Dehaen, W.; Luyten, I.; Toppet. S. Org. Biomol. Chem. 2003, 1, 134. (b) 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.] (c) Shchegolkov, E. V.; Burgart, Ya. V.; Khudina, O. G.; Saloutin, V. I.; Chupakhin, O. N. Russ. Chem. Rev. 2010, 79, 31. [Usp. Khim., 2010, 79, 33.] (d) Elnagdi, M. H.; Sallam, M. M. M.; Fahmy, H. M.; Ibrahim, S. A.-M.; Elias, M. A. M. Helv. Chim. Acta 1976, 59, 551.
(a) Gavkus, D. N.; Maiorova, O. A.; Borisov, M. Yu.; Egorova, A. Yu. Russ. J. Org. Chem. 2012, 48, 1229. [Zh. Org. Khim. 2012, 48, 1230.] (b) Maiorova, O. A.; Borisov, M. Yu.; Egorova, A. Yu. Izv. Sarat. Univ. Nov. Ser. Ser. Khim. Biol. Ekol. 2012, 12(3), 3.
Khattab, S. A.; Shawali, S. A.; Farag, A. M. J. Chem. Eng. Data 1977, 22, 104.
(a) Belskaya, N. P.; Dehaen, W.; Bakulev, V. A. АRKIVOC 2010, (i), 275. (b) Elassar, A.-Z. A.; Dib, H. H.; Al-Awadi, N. A.; Elnagdi M. H. ARKIVOC 2007, (ii), 272.
Allen, F. H.; Kennard, O.; Watson, D. G; Brammer, L.; Orpen,. G.; Taylor; R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
Shvaika, O. P.; Artemov, V. N. Russ. Chem. Rev. 1972, 41, 833. [Usp. Khim. 1972, 41, 1788.]
Weisberger, A.; Proskauer, E.; Riddick, D.; Tupe, E. Organic Solvents [Russian translation]; Izd. Inostr. Lit.: Moscow, 1958, p. 518.
This work was carried out with funding from the Russian Science Fund (grant 15-13-10007) and the Russian Foundation for Basic Research (grant 13-03-00318).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 514–517
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Maiorova, O.A., Babkina, N.V. & Egorova, A.Y. Studies of Stereochemistry of 3-(Arylhydrazono)Furan-2(3Н)-Ones, Synthesis of 4-(Arylhydrazono)Pyridazin-3(1Н)-Ones. Chem Heterocycl Comp 51, 514–517 (2015). https://doi.org/10.1007/s10593-015-1730-5
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DOI: https://doi.org/10.1007/s10593-015-1730-5