Английская Википедия:Friedländer synthesis
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).
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]
The Pfitzinger reaction and the Niementowski quinoline synthesis are variations of the Friedländer reaction.
See also
References
Шаблон:Reflist Шаблон:Organic reactions
- ↑ Organic Syntheses, Coll. Vol. 3, p. 56 (1955); Vol. 28, p. 11 (1948). (Article)
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
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- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
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- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite journal
