- ORIENTATION EFFECTS IN THE SYNTHESIS OF QUINOLINE DERIVATIVES
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The ratio of isomers obtained in the synthesis of quinoline derivatives commencing from m-toluidine and 3,4-dimethylaniline has been studied.Introduction of additional 2- and/or 3-alkyl substituents into the heterocyclic ring has little effect, whilst introduction of a 4-alkyl substituent, either alone or in combination with 2- and/or 3-alkyl groups, causes the proportion of the 5- or 5,6-isomer to fall to zero.In the Beyer synthesis with butanone, 3-condensation predominates, although 1-condensation does occur to a small extent.The quinoline products have been carefully analysed by GLC, NMR and fractional crystallisation techniques, the value of peri-substituent effects in the interpretation of 1H NMR spectra is propounded.
- Osborne, A. G.
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p. 2831 - 2842
(2007/10/02)
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