Friedländer synthesis

Friedländer synthesis

The Friedländer synthesis is the chemical reaction of 2-aminobenzaldehydes [Organic Syntheses, Coll. Vol. 3, p.56 (1955); Vol. 28, p.11 (1948). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0056 Article] )] with ketones to form quinoline derivatives. [Friedländer, P. "Ber." 1882, "15", 2572.] [Friedländer, P.; Gohring, C. F. "Ber." 1883, "16", 1833.] It is named after German chemist Paul Friedländer (1857-1923).

This reaction has been catalyzed by trifluoroacetic acid [Shaabani, A.; Soleimani, E.; Badri, Z. "Synth. Commun." 2007, "37", 629-635. (DOI|10.1080/00397910601055230)] , toluenesulfonic acid [Jia, C.-S.; Zhang, Z.; Tu, S.-J.; Wang, G.-W. "Org. Biomol. Chem." 2006, "4", 104-110.] , iodine [Wu, J.; Xia, H.-G.; Gao, K. "Org. Biomol. Chem." 2006, "4", 126-129.] , and Lewis acids [Varala, R.; Enugala, R.; Adapa, S. R. "Synthesis" 2006, 3825-3830.] .

Several reviews have been published. [Manske, R. H. "Chem. Rev." 1942, "30", 113. (Review)] [Bergstrom, F. W. "Chem. Rev." 1944, "35", 77. (Review)] [Cheng, C. C.; Yan, S. J. "Org. React." 1982, "28", 37. (Review)]

References

ee also

*Doebner-Miller reaction
*Niementowski quinoline synthesis
*Povarov reaction
*Pfitzinger reaction
*Skraup reaction


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