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

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Author(s)
Reynolds, Kristie A
Young, David J
Loughlin, Wendy A
Griffith University Author(s)
Year published
2010
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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 ?-substituted a,߭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 a,߭unsaturated aldehydes.
Journal Title
Synthesis
Volume
21
DOI
Copyright Statement
© 2010 Georg Thieme Verlag. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. The definitive version is available at www.thieme-connect.com
Subject
Analytical chemistry
Organic chemistry
Organic chemical synthesis
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