Synthesis of Substituted Quinolines

  • Author:
  • 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.


Article Views: 1965

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH