128914-79-4Relevant articles and documents
Tautomerism in Ketomethylquinolines. Part 2. Further Results on 2-Ketomethylquinolines
Greenhill, John V.,Loghmani-Khouzani, Hossein,Maitland, Derek J.
, p. 2831 - 2840 (2007/10/02)
A further series of 2-ketomethylquinolines has been prepared, many with α-subbstituents.Base-catalysed α-alkylation of unsubstituted ketomethylquinolines was successful in two instances.With excess sodium hydride and iodomethane α,N-dialkylation occurred. α-Bromination gave three new derivatives which were vulnerable to oxidation to 1,2-diketones.The preparation of two pyrroloquinolines gave model compounds for the enaminone forms of the ketomethylquinolines.Examination of the compounds by IR and NMR spectroscopy has shown that compounds unsubstituted at the α-position and those carrying nitrile or ester groups strongly prefer the enaminone form in solution.The presence of a bromine atom or an alkyl group on the α-carbon gives compounds in which the major or sole tautomer is the ketone.
