Abstract
The reactions of benzamidine, 4-methyl-, 4-iso-butoxy-, and 4-butoxybenzamidine hydrochlorides with chalcone and substituted chalcones in alcohol in the presence of KOH yielded 2,4,6-triarylpyrimidines. 4-Phenyl-2,6-bis(4-methylphenyl)pyrimidine and 1,3-bis(4-phenyl-6-{4-[(E)-styryl]phenyl]pyrimidin-2-yl}benzene) were reacted with (2-chlorophenyl)[(1E)-phenylmethylene]amine in the system KOH/LiH/DMF to give, respectively, 4-phenyl-2,6-bis{4-[(E)-styryl]phenyl}pyrimidine and 1,3-bis(4-phenyl-6-{4-[(E)-styryl]phenyl}pyrimidin-2-yl)benzene.
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REFERENCES
Achelle, S., Malval, J.P., Aloise, S., Barsella, A., Spangenberg, A., Mager, L., Akdas-Kilig, H., Fillaut, J.L., Caro, B., and Robin-Le Guen, F., ChemPhysChem, 2013, vol. 14, p. 2725. https://doi.org/10.1002/cphc.201300419
Svirpa, V.M., Zhang, W., Balia, A.G., Tsodikov, O.V., Nickell, J.R., Gizard, F., Yu, T., Lee, E.Y., Dwoskin, L.P., and Watt, D.S., J. Med. Chem., 2014, vol. 57, p. 6083. https://doi.org/10.1021/jm5004864
Verbitskiy, E.V., Dinastiya, E.M., Baranova, A.A., Khokhlov, K.O. Chuvashov, R.D., Yakovleva, Y.A., Makarova, N.I., Vetrova, E.V., Metelitsa, A.V., Slepukhin, P.A., Rusinov, G.L., Chupakhin, O.N., and Charushin, V.N., Dyes Pigm., 2018, vol. 159, p. 35. https://doi.org/10.1016/j.dyepig.2018.05.075
Harutyunyan, A.A., Panosyan, H.A., Ghukasyan, G.T., and Danagulyan, G.G., Khim. Zh. Arm., 2018, vol. 71, p. 634.
Harutyunyan, A.A., Ghukasyan, G.T., and Danagulyan, G.G., Org. Med. Chem Int. J., 2018, vol. 8, p. 1. https://doi.org/10.19080/OMCIJ.2018.08.555729
Harutyunyan, A.A., Panosyan, H.A., Safaryan, M.S., Harutyunyan, G.K., Gukasyan, G.T., and Danagulyan, G.G., Russ. J. Org. Chem., 2020, vol. 56, p. 269. https://doi.org/10.1134/S1070428020020153
Burdeska, K., Fuhrer, H., Kabas, G., and Siegrist, A.E., Helv. Chim. Acta, 1981, vol. 64, p. 113. https://doi.org/10.1002/hlca.19810640114
Partridge, M.W., J. Chem. Soc., 1949, p. 3043. https://doi.org/10.1039/JR9490003043
Beilst. H, vol. 9, p. 489.
Beilst. H, vol. 7, p. 490.
Beilst. II, vol. 8, p. 227.
Beilst. H, vol. 17, p. 353.
Dodson, R.M. and Seyler, J.K., J. Org. Chem., 1951, vol. 16, p. 461. https://doi.org/10.1021/jo01143a020
Sint. Org. Prep., 1949, vol. 1, p. 75.
Beilst. H, vol. 9, p. 836.
Funding
The work was financially supported by the State Committee for Science of the Republic of Armenia through targeted funding (project no. 18T-1D249) and by the Ministry of Education and Science of the Russian Federation through a subsidy allocated for funding research at the Russian-Armenian University.
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Harutyunyan, A.A., Panosyan, H.A. & Danagulyan, G.G. Novel Pyrimidines with Extended π-Conjugated Chains. Russ J Org Chem 56, 1952–1957 (2020). https://doi.org/10.1134/S1070428020110093
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DOI: https://doi.org/10.1134/S1070428020110093
Keywords:
- arylamidines
- benzene-1,3-dicarboximidamide
- (E)-3-aryl-1-(4-methylphenyl)prop-2-en-1-ones
- 2,4,6-trisubstituted pyrimidines
- (E)-N,1-diphenylmethanimine
- 2,6-bis{4-[(E)-2-phenylvinyl]phenyl}-4-phenylpyrimidine
- 4-(4-methoxyphenyl)-2-phenyl-6-{4-[(E)-2-phenylvinyl]phenyl}pyrimidine
- 2,2'-(1,3-phenylene)bis[4-(4-methylphenyl)-6-phenylpyrimidine]
- 2,2'-(1,3-phenylene)bis(4-phenyl-6-{4-[(E)-2-phenylvinyl]phenyl}pyrimidine)