Studies on the Doebner-Miller, Skraup, and Related Reactions. I. Isolation of Intermediates in the Formation of Quinolines

GM Badger, HP Crocker, BC Ennis, JA Gayler, WE Matthews, WGC Raper, EL Samuel and TM Spotswood

Australian Journal of Chemistry 16(5) 814 - 827
Published: 1963

Abstract

Aniline and substituted anilines have been found to react, in acid solution, with αβ-unsaturated carbonyl compounds (or with substances which can be converted into αβ-unsaturated carbonyl compounds by acid) to give β-arylaminoaldehydes or ketones (IV, VIII, X), or in some cases the anil of a β-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.

Full text doi:10.1071/CH9630814

© CSIRO 1963