Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 51, Issue 3, Pages 250-258Publisher
SPRINGER
DOI: 10.1007/s10593-015-1693-6
Keywords
1,8-bis(dimethylamino)naphthaline; 6-methoxy-N-2,N-2,N-4,N-4,N-5,N-5-hexamethylquinoline-2,4,5-triamine; 4-chloro-5-nitroquinoline; aminodehalogenation; nitration; proton sponge
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Funding
- Russian Foundation for Basic Research [14-03-00010]
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[GRAPHICS] 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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