3-Phenyl/Pyridinyl Derivatives of <i>Trans</i>-2-(aryl/heteryl)vinyl-3<i>H</i>-quinazolin-4-ones: Synthesis and Fluorescent Properties — Oak Academic Publishing
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3-Phenyl/Pyridinyl Derivatives of <i>Trans</i>-2-(aryl/heteryl)vinyl-3<i>H</i>-quinazolin-4-ones: Synthesis and Fluorescent Properties
Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University, Ekaterinburg, Russia
,
Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University, Ekaterinburg, Russia
,
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia
,
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia
,
Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia
,
Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University, Ekaterinburg, Russia
1 Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University, Ekaterinburg, Russia
2 Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University, Ekaterinburg, Russia
3 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia
4 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia
5 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russia
6 Department of Organic Chemistry, Chemical Technology Institute, Urals Federal University, Ekaterinburg, Russia
Novel 3-phenyl/pyridinyl- trans -2-(aryl/heteryl)vinyl-3 H -quinazolin-4-ones 3a,b, 4a, 5a, 7a and their 6,7-difluoro de- rivatives 3c,d, 4b, 5b, 7b have been obtained by condensation of the correspondent 2-methylquinazolin-4-ones 1, 6 with aromatic (heterocyclic) aldehydes in the presence of ZnCl2 (AcONa) or by the reaction of 2-methyl-3,1-benzoxazin-4- ones 2 with the Shiff bases. Effects of aryl(heteryl) substituents on photophysical properties of (aryl/heteryl) quinazolinylethenes have been studied.
KeywordsStyryl BenzazinesFluorinated Quinazolin-4-OnesUV and FL SpectraX-Ray<i>Trans-cis</i>-Isomerisation2-Methylquinazolinones2-Methyl-31-benzoxazinones
A. P. deSilva, H. Q. Gunarantne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, “Signaling Recognition Events with Fluorescent Sensors and Switches,” Chemical Reviews, Vol. 97, No 5, 1997, pp. 1515-1566. doi:10.1021/cr960386p
S. A. Haroutounian and J. A. Katzenellenbogen, “4-Hydro-xystyryldiazines: Synthesis and Fluorescence Properties,” Tetrahedron, Vol. 51, No 6, 1995, pp. 1585-1598. doi:10.1016/0040-4020(94)01050-A
P. H. Bong, H. J. Kim, K. H. Chae, S. C. Shin, N. Naka-shima and K. Yoshihara, “Photochemical Transcis Isom-erization of 1,2-Bis(heteroaryl)ethylenes: 1,2-Bis(py-raz- inyl)ethylene,” Journal of the American Chemical Society, Vol. 108, No 5, 1986, pp. 1006-1014. doi:10.1021/ja00265a027
T. L. Fevig, J. E. Lloyd, J. A. Zablocki and J. A. Katzenel- lenbogen, “Preparation, Receptor Binding, and Fluores-cence Properties of Hexestrol Fluorophore Conjugates: Evaluation of Site of Attachment, Fluorophore Structure, and Fluorophore-Ligand Spacing,” Journal of Medicinal Chemistry, Vol. 30, No. 1, 1987, pp. 156-165. doi:10.1021/jm00384a026
B. R. Kim, S. D. Cho, H. G. Lee, H. S. Yim, M. J. Kim, J. Hwang, S. E. Park, J. J. Kim, K. J. Jung and Y. J. Yoon, “Substituent-Dependence of Photophysical Properties of Trans-2-Styrylpyridazin-3-(2H)-ones,” Journal of Heterocyc- lic Chemistry, Vol. 46, No. 4, 2009, pp. 691-701. doi:10.1002/jhet.137
K. M. K. Swamy, M. S. Park, S. J. Han, S. K. Kim, J. H. Kim, C. Lee, H. Bang, Y. Kim, S. J. Kim and J. Yoon, “New Pyrrolopyridazine Derivatives as Blue Organic Luminophors,” Tetrahedron, Vol. 61, No. 43, 2005, pp. 10227-10234. doi:10.1016/j.tet.2005.08.038
S. Achelle, I. Nouira, B. Pfaffinger, Y. Ramondenc, N. Ple and J. Rodr?guez-Lopez, “V-Shaped 4,6-Bis-(arylvinyl)-pyrimidine Oligomers: Synthesis and Optical Properties,” The Journal of Organic Chemistry, Vol. 74, No. 10, 2009, pp. 3711-3717. doi:10.1021/jo900107u
S. M. Bakalova, A. G. Santos, I. Timcheva, J. Kaneti, I. L. Filipova, G. M. Dobrikov and V. D. Dimitrov, “Electronic Absorption and Emission Spectra and Computational Studies of Some 2-Aryl, 2-Styryl, and 2-(4-Aryl)buta- dienyl quinazolin-4-ones,” Journal of Molecular Structure (Theochem), Vol. 710, 2004, pp. 229-234. doi:10.1016/j.theochem.2004.07.037
B. Bachowska and G. Matusiak, “Synthesis of a New Conjugated 2,2′-(1,4-Phenylenedivinylene)bis-quinoxaline and a Series of Styryl Derivatives of Quinoxaline and Quinoline as Promising Electro-and Photoluminescent Materials,” Chemistry of Heterocyclic Compounds, Vol. 45, No. 1, 2009, pp. 80-84. doi:10.1007/s10593-009-0229-3
I. N. Kang, H. K. Shim and T. Zyung, “Yellow- Light-Emitting Fluorine-Substituted PPV Derivative,” Chemistry of Materials, Vol. 9, No. 3, 1997, pp. 746-749. doi:10.1021/cm960455g
R. M. Gurge, A. M. Sarker, P. M. Lahti, B. Hu and F. E. Karasz, “Light Emitting Properties of Fluorine-Substituted Poly(1,4-phenylene vinylenes),” Ma-cromolecules, Vol. 30, No. 26, 1997, pp. 8286-8292. doi:10.1021/ma970693c
T. V. Trashakhova, E. V. Nosova, M. S. Valova, P. A. Slepukhin, G. N. Lipunova and V. N. Charushin, “Synthesis and Photophysical Properties of 2-Styrylquinazolin-4-ones,” Russian Journal of Organic Chemistry, Vol. 47, No. 5, 2011, pp. 753-761. doi:10.1134/S1070428011050150
F. Liang, J. Chen, Y. Cheng, L. Wang, D. Ma, X. Jing and F. Wang, “Synthesis, Characterization, Photolumi-Nescent and Electroluminescent Properties of New Con- jugated 2,2’-(Arylenedivinylene)bis-8-substituted Quinolines,” Journal of Materials Chemistry, Vol. 13, No. 6, 2003, pp. 1392-1399. doi:10.1039/b210408c
C. C. Chen, K. Pan, S. L. Wang and T. I. Ho, “Styrylthio phene-Amine Exciplexes,” Journal of Luminescence, Vol. 71, No. 4, 1997, pp. 321-328. doi:10.1016/S0022-2313(97)00092-6
S. L. Wang and T. I. Ho, “Substituent Effects on In- tramolecular Charge-Transfer Behaviour of Styrylheterocy- cles,” Journal of Photochemistry and Photobiology. A: Chemistry, Vol. 135, No. 2-3, 2000, pp. 119-126. doi:10.1016/S1010-6030(00)00289-6
O. K. Kim, A. Fort, M. Barzoukas, M. Blanchard-Desee and J. M. Lehn, “Nonlinear Optical Chromophores Containing Dithienothiophene as a New Type of Electron Relay,” Journal of Materials Chemistry, Vol. 9, 1999, pp. 2227-2232. doi:10.1039/a902297j
F. Würthner, F. Effenberger, R. Wortmann and P. Kr?mer, “Second-Order Polarizability of Donor—Acceptor Sub- stituted Oligothiophenes: Substituent Variation and Con- jugation Length Dependence,” Chemical Physics, Vol. 173, No. 2, 1993, pp. 305-314. doi:10.1016/0301-0104(93)80147-2
G. M. Xia, P. Lu, X. G. Xu and G. B. Xu, “Linear and Nonlinear Luminescence Properties of Bithiophene Based Materials,” Optical Materials, Vol. 27, No. 1, 2004, pp. 109-113. doi:10.1016/j.optmat.2004.02.022
M. Thelakkat and H. W. Schmidt, “Low Molecular Weight and Polymeric Heterocyclics as Electron Tran- sport/Hole-Blocking Materials in Organic Light-Emitting Diodes,” Polymers for Advanced Technologies, Vol. 9, No. 7, 1998, pp. 429-442. doi:10.1002/(SICI)1099-1581(199807)9:7 3.0.CO;2-E
B. Jedrzejewska, M. Pietrzak and J. Pacz-kowski, “Solvent Effects on the Spectroscopic Properties of Styrylquinolin- ium Dyes Series,” Journal of Fluorescence, Vol. 20, No. 1, 2010, pp. 73-86. doi:10.1007/s10895-009-0524-5
W. A. E. Omar and O. E. O. Hormi, “Synthesis of 4-(2-Arylvinyl)-8-hydroxyquinolines via Anhydrous Heck Coupling Reaction and the PL Properties of Their Al Complexes,” Tetrahedron, Vol. 65, No. 22, 2009, pp. 4422-4428. doi:10.1016/j.tet.2009.03.028
B. Yin, F. Niemeyer, J. A. G. Williams, J. Jiang, A. Boucekkine, L. Toupet, H. L. Bozec and V. Guerchais, “Synthesis, Structure, and Photophysical Properties of Luminescent Platinum(II) Complexes Containing Cyclometalated 4-Styryl-Functionalized 2-Phenylpyridine Li- gands,” Inorganic Chemistry, Vol. 45, No. 21, 2006, pp. 8584-8596. doi:10.1021/ic0607282
W. H. Melhuish, “Quantum Efficiencies of Fluorescence of Organic Substances: Effect of Solvent Concentration of the Fluorescent Solute,” The Journal of Physical Chemistry, Vol. 65, No. 2, 1961, pp. 229-235. doi:10.1021/j100820a009
G. M. Sheldrick. “A Short History of SHELX,” Acta Crystallo-graphica, Section A, Vol. 64, No. 1, 2008, pp. 112-122. doi:10.1107/S0108767307043930
J. A. Chong, C. Fander, G. R. Larsen, W. C. Lumma, M. M. Moran, A. Ripka, D. J. Underwood, M. Weigele and X. Zhen, “Compounds for Mod-ulating TRPV3 Function,” Chemical Abstracts, Vol. 147, 2007, Article ID: 422361f.
A. A. Laeva, E. V. Nosova, A. V. Golovchenko, N. Yu. Adonin, V. N. Parmon, G. N. Lipunova and V. N. Charushin, “Fluorine-Containing Heterocycles: XIX. Synthesis of Fluorine-Containing Quinazolin-4-ones from 3,1- Benzoxazin-4-ones,” Russian Journal of Organic Chemistry, Vol. 45, No. 6, 2009, pp. 913-920. doi:10.1134/S1070428009060190
B. Dash, E. K. Dora and C. S. Panda, “Synthesis of Some New 2-Aryl-3-Hetaryl-4(3H)Quinazolones,” Journal of the Indian Chemical Society, Vol. 57, No. 8, 1980, pp. 835-836.