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Synthesis of 6-methoxy-N2,N2,N4,N4,N5,N5-hexamethylquinoline- 2,4,5-triamine – a new representative of quinoline proton sponges

Ольга В. Дябло, Александр Ф. Пожарский, Елена А. Шмойлова, Алексей О. Савченко
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Abstract


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-N2,N2,N4,N4-tetramethyl-5nitroquinoline-2,4-diamine with subsequent methylation gave 6-methoxy-N2,N2,N4,N4,N5,N5-hexamethylquinoline-2,4,5-triamine, a new representative of quinoline proton sponges.

How to Cite
Dyablo, O. V.; Pozharskii, A. F.; Shmoilova, E. A.; Savchenko, A. O. Chem. Heterocycl. Compd. 2015, 51, 250. [Khim. Geterotsikl. Soedin. 2015, 51, 250.]

For this article in the English edition see DOI 10.1007/s10593-015-1693-6

 


Keywords


1,8-bis(dimethylamino)naphthaline; 6-methoxy-N2,N2,N4,N4,N5,N5-hexamethylquinoline-2,4,5-triamine; 4chloro-5-nitroquinoline; aminodehalogenation; nitration; proton sponge

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