Abstract
The reactions of quinazoline with 1,3,5-trimethoxybenzene, 3- and 4-methylbenzene-1,2-diamines, and 1-(4-methoxybenzylidene)-2-phenylhydrazine on heating in the presence of trifluoroacetic acid afforded the corresponding stable C–C σ-adducts.
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References
Aniszewski, T., Alkaloids: Chemistry, Biology, Ecology, and Applications, Amsterdam: Elsevier, 2015.
Alafeefy, A., Kadi, A., El-Azab, A., Abdel-Hamid, S., and Daba, M., Arch. Pharm., 2008, vol. 34, p. 377. https://doi.org/10.1107/S1600536813016127
Al-Obaid, A., Abdel-Hamid, S., El-Kashef, H., Abdel Aziz, A., El-Azab, A., Al-Khamees, H., and El-Subbagh, H., Eur. J. Med. Chem., 2009, vol. 44, p. 2379. https://doi.org/10.1016/j.ejmech.2008.09.015
Werbel, L. and Degnan, M., J. Med. Chem., 1987, vol. 30, p. 2151. https://doi.org/10.1021/jm00394a038
Kabri, Y., Azas, N., and Dumetre, A., Eur. J. Med. Chem., 2010, vol. 45, p. 616. https://doi.org/10.1016/j.ejmech.2009.11.005
Kashaw, S., Jatav, V., Mishra, P., Jain, N., and Stable, J., Eur. J. Med. Chem., 2009, vol. 44, p. 4335. https://doi.org/10.1016/j.ejmech.2009.05.008
Jatav, V., Mishra, P., Kashaw, S., and Stables, J., Eur. J. Med. Chem., 2008, vol. 43, p. 1945. https://doi.org/10.1016/j.ejmech.2007.12.003
Al-Shamary, D., Al-Alshaikh, M., Kheder, N., Mabkhot, Y., and Badshah, S., Chem. Cent. J., 2017, vol. 11, p. 1. https://doi.org/10.1186/s13065-017-0272-6
Al-Alshaikh, M., Al-Shammary, D., and El-Baih, F., Res. J. Chem. Environ., 2013, vol. 17, p. 48. https://doi.org/10.1007/s11164-018-3612-9
Ram, V., Farhanullah, B., and Srivastava-Tripathi, A., Bioorg. Med. Chem., 2003, vol. 11, p. 2439. https://doi.org/10.1016/S0968-0896(03)00142-1
Khan, I., Zaib, S., Batool, S., Abbas, N., Ashraf, Z., Iqbal, J., and Saee, A., Bioorg. Med. Chem., 2016, vol. 24, p. 2361. https://doi.org/10.1016/j.bmc.2016.03.031
Pilicheva, T.L., Chupakhin, O.N., and Postovskii, I.Ya., Chem. Heterocycl. Compd., 1975, vol. 11, p. 496. https://doi.org/10.1007/BF00502444
Azev, Yu.A., Shorshnev, S.V., and Golomozin, B.V., Tetrahedron Lett., 2009, vol. 50, p. 2899. https://doi.org/10.1016/j.tetlet.2009.03.199
Matern, A.I., Doctoral (Chem.) Dissertation, Yekaterinburg, 2007.
Rene, O., Souverneva, A., Magnuson, S., and Fauber, B.P., Tetrahedron Lett., 2013, vol. 54, p. 201.
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This study was performed under financial support by the Russian Foundation for Basic Research (project no. 18-33-00 727 mol_a).
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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 12, pp. 1854–1858.
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Azev, Y.A., Koptyaeva, O.S., Seliverstova, E.A. et al. Synthesis of Stable σ-Adducts by Arylation of Quinazoline. Russ J Gen Chem 89, 2374–2377 (2019). https://doi.org/10.1134/S1070363219120089
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DOI: https://doi.org/10.1134/S1070363219120089