Camps quinoline synthesis
Camps quinoline synthesis | |
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Named after | Rudolph Camps |
Reaction type | Ring forming reaction |
Identifiers | |
RSC ontology ID | RXNO:0000524 |
The Camps quinoline synthesis (also known as the Camps cyclization) is a chemical reaction whereby an o-acylaminoacetophenone is transformed into two different hydroxyquinolines (products A and B) using hydroxide ion.[1][2][3][4]
The relative proportions of the hydroxyquinolines (A and B) produced are dependent upon the reaction conditions and structure of the starting material. Although the reaction product is commonly depicted as a quinoline (the enol form), it is believed that the keto form predominates in both the solid state and in solution, making the compound a quinolone.[5]
An example of the Camps reaction is given below:[5]
The amides of 1,3-enaminoketones react to form pyridinones-2 under similar conditions. [6]
References
- ^ Camps, R.; Ber. 1899, 22, 3228.
- ^ Camps, R.; Arch. Pharm. 1899, 237, 659.
- ^ Camps, R.; Arch. Pharm. 1901, 239, 591.
- ^ Manske, R. H. F.; Chem. Rev. 1942, 30, 127. (Review)
- ^ a b Sequential Cu-Catalyzed Amidation-Base-Mediated Camps Cyclization: A Two-Step Synthesis of 2-Aryl-4-quinolones from o-Halophenones Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem.; (Article); 2007; 72(21); 7968-7973. doi:10.1021/jo701384n
- ^ Camps Reaction and Related Cyclizations. A. S. Fisyuk, A. S. Kostyuchenko, D. S. Goncharov. Russ. J. Org. Chem., 2020, 56, (11), 1649–1679 (Review). doi:10.1134/s1070428020110019
See also
- Conrad-Limpach synthesis
- Doebner reaction
- v
- t
- e
- Addition reaction
- Elimination reaction
- Polymerization
- Reagents
- Rearrangement reaction
- Redox reaction
- Regioselectivity
- Stereoselectivity
- Stereospecificity
- Substitution reaction
- A value
- Alpha effect
- Annulene
- Anomeric effect
- Antiaromaticity
- Aromatic ring current
- Aromaticity
- Baird's rule
- Baker–Nathan effect
- Baldwin's rules
- Bema Hapothle
- Beta-silicon effect
- Bicycloaromaticity
- Bredt's rule
- Bürgi–Dunitz angle
- Catalytic resonance theory
- Charge remote fragmentation
- Charge-transfer complex
- Clar's rule
- Conformational isomerism
- Conjugated system
- Conrotatory and disrotatory
- Curtin–Hammett principle
- Dynamic binding (chemistry)
- Edwards equation
- Effective molarity
- Electromeric effect
- Electron-rich
- Electron-withdrawing group
- Electronic effect
- Electrophile
- Evelyn effect
- Flippin–Lodge angle
- Free-energy relationship
- Grunwald–Winstein equation
- Hammett acidity function
- Hammett equation
- George S. Hammond
- Hammond's postulate
- Homoaromaticity
- Hückel's rule
- Hyperconjugation
- Inductive effect
- Kinetic isotope effect
- LFER solvent coefficients (data page)
- Marcus theory
- Markovnikov's rule
- Möbius aromaticity
- Möbius–Hückel concept
- More O'Ferrall–Jencks plot
- Negative hyperconjugation
- Neighbouring group participation
- 2-Norbornyl cation
- Nucleophile
- Kennedy J. P. Orton
- Passive binding
- Phosphaethynolate
- Polar effect
- Polyfluorene
- Ring strain
- Σ-aromaticity
- Spherical aromaticity
- Spiroaromaticity
- Steric effects
- Superaromaticity
- Swain–Lupton equation
- Taft equation
- Thorpe–Ingold effect
- Vinylogy
- Walsh diagram
- Woodward–Hoffmann rules
- Woodward's rules
- Y-aromaticity
- Yukawa–Tsuno equation
- Zaitsev's rule
- Σ-bishomoaromaticity