Abstract
Alkylation of 4,8-dimethyl- and 4,6,8-trimethylquinolin-2(1H)-one with allyl bromide in the presence of a base proceeds at the oxygen and nitrogen atoms with the predominant formation of the O-isomer. The reaction of 2-allyloxyquinolines with halogens leads to the formation of oxazolo[3,2-a]quinolinium salts. Structure of 1-bromomethyl-5,7,9-trimethyl-1,2-dihydro[1,3]oxazolo[3,2-a]quinolinium iododibromide was established by single crystal X-ray diffraction method.
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References
Charushin, V.N., Nosova, E.V., Lipunova, G.N., and Chupakhin, O.N., Ftorkhinolony: sintez i primenenie (Fluo-roquinolones: synthesis and application), Moscow: FIZ-MATLIT, 2013. p. 24.
Aly, A.A., El-Sheref, E.M., Mourad, A.F.E., Bakheet, M.E., and Bräse, S., Mol. Diversity, 2019. https://doi.org/10.1007/s11030-019-09952-5
Joule, J.A. and Mills, K., Heterocyclic Chemistry, Wiley-Blackwell, 2010.
Gyul’budagyan, L.V., Aleksanyan, I.I., and Avetisyan, A.A., Arm. Khim. Zh., 1989, vol. 42, no. 10, p. 636.
Onysko, M.Yu. and Lendel, V.G., Chem. Heterocycl. Compd., 2007, vol. 43, no. 8, p. 1020. https://doi.org/10.1007/s10593-007-0159-x
Vershinina, E.A. and Kim, D.G., Vestn. YuUrGU, Ser. Khim., 2010, no. 31, p. 10.
Kim, D.G., Sashin, A.V., Kozlovskaya, V.A., and Andreeva, I.N., Chem. Heterocycl. Compd., 1996, vol. 32, no. 9, p. 1075. https://doi.org/10.1007/BF01164715
Ukrainets, I.V., Bereznyakova, N.L., Parshi-kov, V.A., and Turov, A.V., Chem. Heterocycl. Compd., 2007, vol. 43, no. 10, p. 1269. https://doi.org/10.1007/s10593-007-0193-8
Kim, D.G., Vershinina, E.A., Ovchinnikova, I.G., Slepu-khin, P.A., Ezhikova, M.A., and Kodess, M.I., Chem. Heterocycl. Compd., 2018, vol. 54, no. 10, p. 977. https://doi.org/10.1007/s10593-018-2374-z
Gorlov, M., Pettersson, H., Hagfeldt, A., and Kloo, L., Inorg. Chem., 2007, vol. 46, no. 9, p. 3566. https://doi.org/10.1021/ic062244b
Chernov’yants, M.S., Burykin, I.V., Berezova, P.N., and Starikova, Z.A., Mendeleev Commun., 2010, vol. 20, no. 3, p. 182. https://doi.org/10.1016/j.mencom.2010.05.021
Chernov’yants, M.S., Burykin, I.V., and Aleshina, N., Russ. J. Gen. Chem., 2008}, vol. 78, no. 7}, p. 1345. https://doi.org/10.1134/S1070363208070104
SMART and SAINT-Plus, Versions 5.0, Bruker AXS Inc., Madison, WI, USA, 1998.
SHELXTL/PC, Versions 5.10, Bruker AXS Inc., Madison, WI, USA, 1998.
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 12, pp. 1829–1834.
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Kim, D.G., Vershinina, E.A. & Sharutin, V.V. Synthesis and Halogenocyclization of 2-Allyloxyquinoline Derivatives. Russ J Gen Chem 89, 2353–2357 (2019). https://doi.org/10.1134/S1070363219120041
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DOI: https://doi.org/10.1134/S1070363219120041