Английская Википедия:Friedländer synthesis

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Шаблон:Use dmy dates Шаблон:Reactionbox 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 trifluoroacetic acid,[4] toluenesulfonic acid,[5] iodine,[6] and Lewis acids.[7]

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

Mechanism

Two viable reaction mechanisms exist for this reaction. In the first mechanism 2-amino substituted carbonyl compound 1 and carbonyl compound 2 react in a rate-limiting step to aldol adduct 3. This intermediate loses water in an elimination reaction to 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

Шаблон:Reflist Шаблон:Organic reactions