| 词条 | Friedländer synthesis |
| 释义 |
| Name = Friedländer synthesis | Type = Ring forming reaction | NamedAfter = Paul Friedländer | Section3 = {{Reactionbox Identifiers | OrganicChemistryNamed = 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). 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] MechanismTwo 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
References1. ^Organic Syntheses, Coll. Vol. 3, p. 56 (1955); Vol. 28, p. 11 (1948). (Article) {{DEFAULTSORT:Friedlander synthesis}}2. ^{{cite journal|author=Friedländer, P. |journal=Chemische Berichte|year=1882|volume=15|pages= 2572–2575|doi=10.1002/cber.188201502219|title=Ueber o-Amidobenzaldehyd|issue=2}} 3. ^{{cite journal|author1=Friedländer, P. |author2=Gohring, C. F. |journal=Ber.|year=1883|volume=16|pages= 1833–1839|doi=10.1002/cber.18830160265|title=Ueber eine Darstellungsmethode im Pyridinkern substituirter Chinolinderivate|issue=2}} 4. ^{{cite journal|author1=Shaabani, A. |author2=Soleimani, E. |author3=Badri, Z. |doi=10.1080/00397910601055230|title=Triflouroacetic Acid as an Efficient Catalyst for the Synthesis of Quinoline|year=2007|journal=Synthetic Communications|volume=37|issue=4|pages=629–635}} 5. ^{{cite journal|author1=Jia, C.-S. |author2=Zhang, Z. |author3=Tu, S.-J. |author4=Wang, G.-W. |journal=Org. Biomol. Chem.|year=2006|volume=4|pages= 104–110|doi=10.1039/b513721g|title=Rapid and efficient synthesis of poly-substituted quinolines assisted by p-toluene sulphonic acid under solvent-free conditions: Comparative study of microwave irradiation versus conventional heating}} 6. ^{{cite journal|author1=Wu, J. |author2=Xia, H.-G. |author3=Gao, K. |journal=Org. Biomol. Chem.|year=2006|volume=4|pages= 126–129|doi=10.1039/b514635f|title=Molecular iodine: A highly efficient catalyst in the synthesis of quinolines via Friedländer annulation}} 7. ^{{cite journal|author1=Varala, R. |author2=Enugala, R. |author3=Adapa, S. R. |journal=Synthesis|year=2006|pages= 3825–3830 | doi = 10.1055/s-2006-950296 |volume=2006 |title=Efficient and Rapid Friedlander Synthesis of Functionalized Quinolines Catalyzed by Neodymium(III) Nitrate Hexahydrate}} 8. ^{{cite journal|author=Manske, R. H. |journal=Chem. Rev.|year=1942|volume=30|pages= 113–144|doi=10.1021/cr60095a006|title=The Chemistry of Quinolines}} 9. ^{{cite journal|author=Bergstrom, F. W. |journal=Chem. Rev.|year=1944|volume=35|pages= 77–277|doi=10.1021/cr60111a001|title=Heterocyclic Nitrogen Compounds. Part IIA. Hexacyclic Compounds: Pyridine, Quinoline, and Isoquinoline|issue=2}} 10. ^{{cite book|author1=Cheng, C.-C. |author2=Yan, S.-J. |doi=10.1002/0471264180.or028.02|chapter=The Friedländer Synthesis of Quinolines|title=Organic Reactions|year=2004|isbn=0471264180}} 11. ^{{cite journal|author1=Jose Marco-Contelles |author2=Elena Perez-Mayoral |author3=Abdelouahid Samadi |author4=Marıa do Carmo Carreiras |author5=Elena Soriano |title=Recent Advances in the Friedlander Reaction|doi=10.1021/cr800482c|year=2009|journal=Chemical Reviews|volume=109|issue=6|pages=2652–71|pmid=19361199}} 3 : Condensation reactions|Quinoline forming reactions|Name reactions |
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