Abstract
An efficient approach to the synthesis of 2-(5-arylpyridin-2-yl)quinolines containing fluorine atoms and a cyclopentene fragment was suggested. Photophysical properties of new compounds were studied and compared to those of the earlier described compounds without such functional groups.
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S. Donga, W. Wanga, Synth. Met., 2009, 159, 385.
T. V. Trashakhova, E. V. Nosova, M. S. Valova, P. A. Slepukhin, G. N. Lipunova, V. N. Charushin, Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 753 [Zh. Org. Khim., 2011, 47, 748].
D. S. Kopchuk. PhD Thesis (Chem.), UGTU-UPI, Ekaterinburg, 2010, 122 pp. (in Russian).
V. N. Kozhevnikov, Y. Zheng, M. Clough, H. A. Al-Attar, G. C. Griffiths, K. Abdullah, S. Raisys, V. Jankus, M. R. Bryce, A. P. Monkman, Chem. Mater., 2013, 25, 2352.
L. S. Hung, C. H. Chen, Mater. Sci. Eng., 2002, 39, 143 (and references cited therein).
N. Liu, M. M. Shi, Y. Z. Li, Y. W. Shi, G. Z. Ran, G. G. Qin, M. Wang, H. Z. Chen, J. Lumin., 2011, 131, 199–205.
Y. Huo, J. Lu, T. Lu, X. Fang, X. Ouyang, L. Zhang, G. Yuan, New J. Chem., 2015, 39, 333.
M. Irie, T. Fukaminato, K. Matsuda, S. Kobatake, Chem. Rev., 2014, 114, 12174.
K. K. Kartha, S. S. Babu, S. Srinivasan, A. Ajayaghosh, J. Am. Chem. Soc., 2012, 134, 4834.
G. V. Zyryanov, D. S. Kopchuk, I. S. Kovalev, E. V. Nosova, V. L. Rusinov, O. N. Chupakhin, Russ. Chem. Rev., 2014, 83, 783.
V. V. Kouznetsov, L. Y. Vargas Méndez, C. M. Meléndez Gomez, Curr. Org. Chem., 2005, 9, 141.
A. Shirai, O. Miyata, N. Tohnai, M. Miyata, D. J. Procter, D. Sucunza, T. Naito, J. Org. Chem., 2008, 73, 4464.
T. Shigeyama, K. Katakama, M. Kitajima, H. Takayama, Org. Lett., 2007, 9, 4069.
D. Keck, S. Vanderheiden, S. Braese, Eur. J. Org. Chem., 2006, 21, 4916.
H. Kagoshima, T. Akiyama, Org. Lett., 2000, 2, 1577.
L. Strekowski, H. Lee, J. Fluorine Chem., 2000, 104, 281.
B. Crousse, J.-P. Bégué, D. Bonnet-Delpon, J. Org. Chem., 2000, 65, 5009.
C. J. Ohnmacht, A. R. Patel, R. E. Lutz, J. Med. Chem., 1971, 14, 926.
J. L. Mao, B. J. Wan, Y. H. Wang, S. G. Franzblau, A. P. Kozikowski, ChemMedChem, 2007, 2, 811.
A. Lilienkampf, J. L. Mao, B. J. Wan, Y. H. Wang, S. G. Franzblau, A. P. Kozikowski, J. Med. Chem., 2009, 52, 2109.
P. M. O´Neill, R. C. Storr, B. K. Park, Tetrahedron, 1998, 54, 4615.
R. E. Banks, B. E. Smart, J. C. Tatlow, Organofluorine Chemistry, Principles and Commercial Applications, Plenum Press, New York, 1994, 644 p.
H. A. Qaseer, A. K. El-Qisairia, M. H. Zaghal, Z. Anorg. Allg. Chem., 2006, 632, 343.
G. Maayan, Y. Dayagi, R. Arad-Yellin, L. J. W. Shimon, A. Shanzer, Polyhedron, 2013, 64, 365.
H. A. Qaseer, Croat. Chem. Acta, 2005, 78, 79.
V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. König, D. N. Kozhevnikov, Tetrahedron, 2008, 64, 8963.
D. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, P. A. Slepukhin, V. N. Kozhevnikov, Tetrahedron Lett., 2006, 47, 7025.
I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 536 [Khim. Geterotsikl. Soedin., 2012, 576].
D. S. Kopchuk, I. L. Nikonov, G. V. Zyryanov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 907 [Khim. Geterotsikl. Soedin., 2014, 983].
A. M. Prokhorov, D. N. Kozhevnikov, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 1163 [Khim. Geterotsikl. Soedin., 2012, 1237].
D. S. Kopchuk, I. S. Kovalev, A. F. Khasanov, G. V. Zyryanov, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin, Mendeleev Commun., 2013, 23, 142.
D. N. Kozhevnikov, V. N. Kozhevnikov, M. M. Ustinova, A. Santoro, D. W. Bruce, B. Koenig, R. Czerwieniec, T. Fischer, M. Zabel, H. Yersin, Inorg. Chem., 2009, 48, 4179.
Pat. WO 2004/65389 A1; http://patentscopewipoint/search/ en/search.
V. N. Kozhevnikov, M. M. Ustinova, P. A. Slepukhin, A. Santoro, D. W. Bruce, D. N. Kozhevnikov, Tetrahedron Lett., 2008, 49, 4096.
W. H. Melhuish, J. Phys. Chem., 1961, 65, 229.
B. B. Dey, J. Chem. Soc., 1914, 105, 1039.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0872–0877, April, 2015.
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Kopchuk, D.S., Khasanov, A.F., Kim, G.A. et al. Functionalized 2-(5-arylpyridin-2-yl)quinolines: synthesis and photophysical properties. Russ Chem Bull 64, 872–877 (2015). https://doi.org/10.1007/s11172-015-0947-x
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DOI: https://doi.org/10.1007/s11172-015-0947-x