Friedländer synthesis

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Friedländer synthesis
Named after Paul Friedländer
Reaction type Ring forming reaction
Identifiers
Organic Chemistry Portal friedlaender-synthesis

The Friedländer synthesis is a chemical reaction of 2-aminobenzaldehydes[1] with ketones to form quinoline derivatives.[2][3] It is named after German chemist Paul Friedländer (1857–1923).

The Friedländer synthesis
The Friedländer synthesis

This reaction has been catalyzed by

Lewis acids.[7]

Several reviews have been published.[8][9][10]

Mechanism

Two viable

unsaturated carbonyl compound 4 and then loses water again in imine formation to quinoline 7. In the second mechanism the first step is Schiff base formation to 5 followed by Aldol reaction to 6 and elimination to 7.[11]

Friedländer synthesis reaction mechanism

The Pfitzinger reaction and the Niementowski quinoline synthesis are variations of the Friedländer reaction.

See also

References

  1. ^ Organic Syntheses, Coll. Vol. 3, p.　56 (1955); Vol. 28, p.　11 (1948). (Article)
  2. doi:10.1002/cber.188201502219
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  3. doi:10.1002/cber.18830160265
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  4. S2CID 98625429
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  5. PMID 16358003
    .
  6. PMID 16358006
    .
  7. doi:10.1055/s-2006-950296
    .
  8. doi:10.1021/cr60095a006
    .
  9. doi:10.1021/cr60111a001
    .
  10. ISBN 0471264180
    .
  11. PMID 19361199
    .
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