Abstract
The method for the synthesis of 7,7,9-trimethyl-6,7-dihydrofuro[3,2-f]quinoline was developed. The parameters characterizing its antioxidant activity, the stoichiometric inhibition factor (f ≈ 3), and the rate constant of the reaction with peroxy radicals (fk 7 = 2.4 · 105 L mol−1 s−1, 60 °C) were determined for the model system of initiated ethylbenzene oxidation. The inhibition stoichiometric factor of furodihydroquinoline is 2, but the colored product formed as a result of its conversion in oxidized hydrocarbons provides the additional inhibition with k 7 = 6.3 · 103 L mol−1 s−1.
Similar content being viewed by others
References
J. Llano, J. Raber, L. A. Eriksson, J. Photochem., Photobiol., A, 2003, 154, 235.
C. Marzano, A. Chilin, F. Bordin, F. Baccichetti, A. Guiotto, Bioorg. Med. Chem., 2002, 10, 2835.
K. Ando, Y. Akai, J. Kunimoto, T. Yokomizo, H. Nakajima, T. Takeuchi, M. Yamashita, S. Ohta, T. Obishi, Y. Obishi, Org. Biomol. Chem., 2007, 5, 655.
T. D. Nekipelova, A. B. Gagarina, N. M. Emanuel, Dokl. Akad. Nauk SSSR, 1976, 226, 626 [Dokl. Phys. Chem. USSR, 1976, 226, Nos 1–3 (Engl. Transl.)].
T. D. Nekipelova, A. B. Gagarina, Neftekhimiya, 1982, 22, 278 [Petroleum Chemistry, 1982, 22, No. 2 (Engl. Transl.)].
O. T. Kasaikina, Vliyanie struktury gidrirovannykh khinolinov na puti prevrashcheniya i reaktsionnuyu sposobnost’ pri vzaimodeistvii so svobodnymi radikalami [Effect of the Structure of Hydrogenated Quinolines on the Transformation Routes and Reactivity in Reactions with Free Radicals], Preprint, Chernogolovka, 1989 (in Russian).
S. Thorisson, F. D. Gunstone, R. Hardy, Chem. Phys. Lipids, 1992, 60, 263.
J. U. Skaare, Xenobiotica, 1979, 11, 659.
P. I. Abramenko, V. G. Zhiryakov, T. K. Ponomareva, Khim. Geterotsikl. Soedin., 1975, 1603 [Chem. Heterocycl. Compd., 1975, 11, 1361 (Engl. Transl.)].
M.-E. Theoclitou, L. A. Robinson, Tetrahedron Lett., 2002, 43, 3907.
V. F. Tsepalov, V. Ya. Shlyapintokh, Kinet. Katal., 1962, 3, 870 [Kinet. Catal., 1962 (in Russian)].
N. M. Emanuel’, G. P. Gladyshev, E. T. Denisov, V. F. Tsepalov, V. V. Kharitonov, K. B. Piotrovskii, Poryadok testirovaniya khimicheskikh soedinenii kak stabilizatorov polimernykh materialov [The Procedure of Testing Chemical Compounds As Stabilizers of Polymeric Materials], Preprint, 1976, Chernogolovka, p. 11 (in Russian).
T. D. Nekipelova, Ya. N. Malkin, V. A. Kuzmin, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 80 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, 29, 67 (Engl. Transl.)].
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2356–2360, November, 2008.
Rights and permissions
About this article
Cite this article
Kuzmin, V.A., Mazaletskaya, L.I., Nekipelova, T.D. et al. Synthesis and antioxidant activity of 7,7,9-trimethyl-6,7-dihydrofuro[3,2-f]quinoline. Russ Chem Bull 57, 2405–2409 (2008). https://doi.org/10.1007/s11172-008-0343-x
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-008-0343-x