Friedländer synthesis: Difference between revisions

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The Friedländer synthesis is the 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]

References

^ Organic Syntheses, Coll. Vol. 3, p.56 (1955); Vol. 28, p.11 (1948). (Article)
^ Friedländer, P. Ber. 1882, 15, 2572.
^ Friedländer, P.; Gohring, C. F. Ber. 1883, 16, 1833.
^ Shaabani, A.; Soleimani, E.; Badri, Z. Synth. Commun. 2007, 37, 629-635. (doi:10.1080/00397910601055230)
^ Jia, C.-S.; Zhang, Z.; Tu, S.-J.; Wang, G.-W. Org. Biomol. Chem. 2006, 4, 104-110.
^ Wu, J.; Xia, H.-G.; Gao, K. Org. Biomol. Chem. 2006, 4, 126-129.
^ Varala, R.; Enugala, R.; Adapa, S. R. Synthesis 2006, 3825-3830.
^ 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)

@@ Line 1: / Line 1: @@
-The [[Friedländer synthesis]] is the [[chemical reaction]] of 2-aminobenzaldehydes{{Ref|Smith1948}} with [[ketone]]s to form [[quinoline]] derivatives.{{Ref|Friedländer1882}}{{Ref|Friedländer1883}} It is named after German chemist [[Paul Friedländer (chemist)|Paul Friedländer]] (1857-1923).
+The [[Friedländer synthesis]] is the [[chemical reaction]] of 2-aminobenzaldehydes<ref>[[Organic Syntheses]], Coll. Vol. 3, p.56 (1955); Vol. 28, p.11 (1948). ([http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0056 Article])</ref> with [[ketone]]s to form [[quinoline]] derivatives.<ref>Friedländer, P. ''[[Ber.]]'' '''1882''', ''15'', 2572.</ref><ref>Friedländer, P.; Gohring, C. F. ''[[Ber.]]'' '''1883''', ''16'', 1833.</ref> It is named after German chemist [[Paul Friedländer (chemist)|Paul Friedländer]] (1857-1923).
 [[Image:Friedlaender Synthesis Scheme.png|center|400px|The Friedländer synthesis]]
+This reaction has been catalyzed by [[trifluoroacetic acid]]<ref>Shaabani, A.; Soleimani, E.; Badri, Z. ''[[Synth. Commun.]]'' '''2007''', ''37'', 629-635. ({{DOI|10.1080/00397910601055230}})</ref>, [[toluenesulfonic acid]]<ref>Jia, C.-S.; Zhang, Z.; Tu, S.-J.; Wang, G.-W. ''[[Org. Biomol. Chem.]]'' '''2006''', ''4'', 104-110.</ref>, [[iodine]]<ref>Wu, J.; Xia, H.-G.; Gao, K. ''[[Org. Biomol. Chem.]]'' '''2006''', ''4'', 126-129.</ref>, and [[Lewis acid]]s<ref>Varala, R.; Enugala, R.; Adapa, S. R. ''[[Synthesis (journal)|Synthesis]]'' '''2006''', 3825-3830.</ref>.
-Several reviews have been published.{{Ref|Manske1942}}{{Ref|Bergstrom1944}}{{Ref|Cheng1982}}
+Several reviews have been published.<ref>Manske, R. H. ''[[Chem. Rev.]]'' '''1942''', ''30'', 113. (Review)</ref><ref>Bergstrom, F. W. ''[[Chem. Rev.]]'' '''1944''', ''35'', 77. (Review)</ref><ref>Cheng, C. C.; Yan, S. J. ''Org. React.'' '''1982''', ''28'', 37. (Review)</ref>
 ==References==
+{{Reflist}}
-# {{Note|Smith1948}} [[Organic Syntheses]], Coll. Vol. 3, p.56 (1955); Vol. 28, p.11 (1948). ([http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0056 Article])
-# {{Note|Friedländer1882}} Friedländer, P. ''[[Ber.]]'' '''1882''', ''15'', 2572.
-# {{Note|Friedländer1883}} Friedländer, P.; Gohring, C. F. ''[[Ber.]]'' '''1883''', ''16'', 1833.
-# {{Note|Manske1942}} Manske, R. H. ''[[Chem. Rev.]]'' '''1942''', ''30'', 113. (Review)
-# {{Note|Bergstrom1944}} Bergstrom, F. W. ''[[Chem. Rev.]]'' '''1944''', ''35'', 77. (Review)
-# {{Note|Cheng1982}} Cheng, C. C.; Yan, S. J. ''Org. React.'' '''1982''', ''28'', 37. (Review)
 ==See also==
+*[[Doebner-Miller reaction]]
 *[[Niementowski quinoline synthesis]]
+*[[Povarov reaction]]
 *[[Pfitzinger reaction]]
+*[[Skraup reaction]]