Doebner quinoline synthesis

What is Doebner quinoline synthesis?

The Doebner quinoline synthesis, also referred to as the Doebner reaction or Döbner reaction, involves the synthesis of substituted cinchoninic acids (quinolines with a carboxylic acid group -COOH) from aromatic amines through a reaction with aldehydes and pyruvic acid upon heating.

Doebner quinoline synthesis - Doebner reaction - Döbner reaction
Doebner quinoline synthesis

References

  • Döbner, O. (1887), 1) Ueber α-Alkylcinchoninsäuren und α-Alkylchinoline. [1) On α-alkylcinchoninic acids and α-alkylquinolines.] Justus Liebigs Ann. Chem., 242: 265-289. https://doi.org/10.1002/jlac.18872420302
  • Doebner, O. (1887), Ueber α-Alkylcinchoninsäuren. [On α-alkylcinechoninic acids.] Ber. Dtsch. Chem. Ges., 20: 277-281. https://doi.org/10.1002/cber.18870200171
  • Doebner, O. (1894), Die Synthese der α-Alkyl-β-naphtocinchoninsäuren, eine specifische Reaction auf Aldehyde, insbesondere zum Nachweis derselben in ätherischen Oelen. [The synthesis of α-alkyl-β-naphtocinchoninic acids, a specific reaction on aldehydes, especially for the detection of the same in essential oils.] Ber. Dtsch. Chem. Ges., 27: 352-354. https://doi.org/10.1002/cber.18940270172
  • Doebner, O. (1894), Ueber die Synthese der α-Alkyl-β-naphtocinchoninsäuren, eine specifische Reaction auf Aldehyde. [On the synthesis of α-alkyl-β-naphtocinchoninic acids, a specific reaction on aldehydes.] Ber. Dtsch. Chem. Ges., 27: 2020-2030. https://doi.org/10.1002/cber.189402702169
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