
%0 Journal Article
%A Badger, GM 
%A Crocker, HP 
%A Ennis, BC 
%A Gayler, JA 
%A Matthews, WE 
%A Raper, WGC 
%A Samuel, EL 
%A Spotswood, TM 
%T Studies on the Doebner-Miller, Skraup, and Related Reactions. I. Isolation of Intermediates in the Formation of Quinolines
%J Australian Journal of Chemistry
%D 1963/10/01
%V 16
%N 5
%P 814-827
%K 
%R https://doi.org/10.1071/CH9630814
%U https://www.publish.csiro.au/paper/CH9630814 
%X Aniline and substituted anilines have been found to react, in acid solution, with &#945;&#946;-unsaturated carbonyl compounds (or with substances which can be converted into &#945;&#946;-unsaturated carbonyl compounds by acid) to give &#946;-arylaminoaldehydes or ketones (IV, VIII, X), or in some cases the anil of a &#946;-arylaminoaldehyde. These adducts have been cyclized, sometimes in good yield, to the corresponding quinolines: and the evidence indicates that compounds of these types must be intermediates m the Skraup, the Doebner-Miller, and related reactions. The mechanisms of these reactions are critically discussed. Satisfactory methods for the preparation of many quinolines have been devised, and syntheses of several new quinolines are reported. 
