We report the synthesis of 4-chloro-2-methyl-5-nitro- and 2,4-dichloro-5-nitroquinolines, containing methoxy groups at positions 6 and 8. The reaction of these compounds with dimethylamine solution in alcohol was shown to produce not only aminodehalogenation products, but also resulted in nucleophilic substitution of the methoxy groups. The reduction of 6-methoxy-N 2,N 2,N 4,N 4-tetramethyl-5-nitroquinoline-2,4-diamine with subsequent methylation gave 6-methoxy-N 2,N 2,N 4,N 4,N 5,N 5-hexamethylquinoline-2,4,5-triamine, a new representative of quinoline proton sponges.
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This work received financial support from the Russian Foundation for Basic Research (project No. 14-03-00010).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(3), 250–258
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Dyablo, O.V., Pozharskii, A.F., Shmoilova, E.A. et al. Synthesis of 6-methoxy-N 2,N 2,N 4,N 4,N 5,N 5-hexamethylquinoline-2,4,5-triamine – a new representative of quinoline proton sponges. Chem Heterocycl Comp 51, 250–258 (2015). https://doi.org/10.1007/s10593-015-1693-6
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DOI: https://doi.org/10.1007/s10593-015-1693-6