:Camps quinoline synthesis

{{Reactionbox

| Name = Camps quinoline synthesis

| Type = Ring forming reaction

| NamedAfter = Rudolph Camps

| Section3 = {{Reactionbox Identifiers

| RSC_ontology_id = 0000524

}}

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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.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)

Image:Camps Quinoline Synthesis Scheme.png

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: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}}

Image:CampsApplication.svg

The amides of 1,3-enaminoketones react to form pyridinones-2 under similar conditions. 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}}