Synthesis of Substituted Quinolines

  • Author: ChemistryViews.org
  • Published: 26 April 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of Organic Chemistry/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Synthesis of Substituted Quinolines

Substituted quinolines are common chemical frameworks in bioactive compounds and useful building blocks in materials science. They could potentially be synthesized by a cyclization of 2-aminostyryl ketone derivatives. However, the more stable (E) configuration these styryls prevents close contact between the anime and the carbonyl group, and thus, the cyclization.


Cheol-Hong Cheon and colleagues, Korea University, Seoul, have used iodide as a catalyst to allow this type of reaction. The team combined 2-aminostyryl ketones with tetrabutylammonium iodide (TBAI) as a nucleophilic catalyst. The iodide is added to the styryl double bond, and the resulting β-iodoketones can adopt a cis-like conformation (pictured top). The amino and carbonyl groups can then undergo a condensation reaction to form a ring. A subsequent elimination of hydrogen iodide provides the desired quinolines (pictured bottom) and regenerates the catalyst.


The reaction is suitable for a variety of 2-aminostyryl ketone substrates and proceeds in excellent yields. In addition, the resulting quinolines can be further transformed without isolation of the product.


 

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