Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines

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

Research output: Contribution to journalArticleResearchpeer-review

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.

Original languageEnglish
Article numberP11410SS
Pages (from-to)3645-3648
Number of pages4
JournalSynthesis
Volume2010
Issue number21
DOIs
Publication statusPublished - Nov 2010
Externally publishedYes

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Quinolines
2-butenal
Aniline
Aldehydes
Aniline Compounds
Complex Mixtures
2-methylquinoline
cinnamic aldehyde
aniline

Cite this

Reynolds, Kristie A. ; Young, David J. ; Loughlin, Wendy A. / Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines. In: Synthesis. 2010 ; Vol. 2010, No. 21. pp. 3645-3648.
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Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines. / Reynolds, Kristie A.; Young, David J.; Loughlin, Wendy A.

In: Synthesis, Vol. 2010, No. 21, P11410SS, 11.2010, p. 3645-3648.

Research output: Contribution to journalArticleResearchpeer-review

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