Camps quinoline synthesis
Encyclopedia
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.
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
.
An example of the Camps reaction is given below :
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
whereby an o-acylaminoacetophenone is transformed into two different hydroxyquinolines (products A and B) using hydroxide
Hydroxide
Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and a hydrogen atom held together by a covalent bond, and carrying a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, as a ligand, a nucleophile, and a...
ion.
reaction conditions and structure of the starting material. Although the reaction product is commonly depicted as a quinoline
Quinoline
Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown...
(the enol form
Keto-enol tautomerism
In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a keto form and an enol . The enol and keto forms are said to be tautomers of each other...
), it is believed that the keto form
Keto-enol tautomerism
In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a keto form and an enol . The enol and keto forms are said to be tautomers of each other...
predominates in both the solid state and in solution, making the compound a quinolone
Quinolone
The quinolones are a family of synthetic broad-spectrum antibiotics. The term quinolone refers to potent synthetic chemotherapeutic antibacterials....
.
An example of the Camps reaction is given below :