Camps quinoline synthesis

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]:

References

  1. ^ Camps, R.; Ber. 1899, 22, 3228.
  2. ^ Camps, R.; Arch. Pharm. 1899, 237, 659.
  3. ^ Camps, R.; Arch. Pharm. 1901, 239, 591.
  4. ^ Manske, R. H. F.; Chem. Rev. 1942, 30, 127. (Review)
  5. ^ 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

See also