
TY  - JOUR
A1  - Badger, GM 
A1  - Crocker, HP 
A1  - Ennis, BC 
A1  - Gayler, JA 
A1  - Matthews, WE 
A1  - Raper, WGC 
A1  - Samuel, EL 
A1  - Spotswood, TM 
T1  - Studies on the Doebner-Miller, Skraup, and Related Reactions. I. Isolation of Intermediates in the Formation of Quinolines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1963
VL  - 16
IS  - 5
SP  - 814
EP  - 827
KW  - 
UR  - https://doi.org/10.1071/CH9630814 
N2  - 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. 
ER  -

