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Camps quinoline synthesis

Lianyungang Klinechem Co.,Ltd | Updated: Dec 03, 2018

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]

Camps quinoline synthesis

References

  1. ^ Camps, R.; Ber. 189922, 3228.

  2. ^ Camps, R.; Arch. Pharm. 1899237, 659.

  3. ^ Camps, R.; Arch. Pharm. 1901239, 591.

  4. ^ Manske, R. H. F.; Chem. Rev. 194230, 127. (Review)

  5. Jump up to: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


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