Limitations of the ‘Two-Phase’ Doebner-Miller
Reaction for the Synthesis of Quinolines

Kristie A. Reynolds; David J. Young; Wendy A. Loughlin

doi:10.1055/s-0030-1258258

PAPER

Limitations of the ‘Two-Phase’ Doebner-Miller Reaction for the Synthesis of Quinolines

Kristie A. Reynolds^a, David J. Young^a,b, Wendy A. Loughlin*^a,c
^a Eskitis Institute for Cell and Molecular Therapies, Nathan Campus, Griffith University, Brisbane, QLD, 4111, Australia
^b School of Biomolecular and Physical Sciences, Nathan Campus, Griffith University, Brisbane, QLD, 4111, Australia
^c Science, Environment, Engineering, and Technology Executive, Nathan Campus, Griffith University, Brisbane, QLD, 4111, Australia
Fax: +61(7)37354307; e-Mail: w.loughlin@griffith.edu.au;

Abstract

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Abstract

The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.

Key words

α,β-unsaturated aldehyde - aniline - quinoline - Doebner-Miller reaction - heterocycle

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References

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