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Thiolate-mediated cyclization yields 2-quinolones from aminocinnamic acids

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A person in a light blue lab coat holds test tubes containing blue and yellow liquids at a laboratory bench with several glass vessels including a round-bottom flask containing blue liquid.
Research area:Organic chemistryOrganic ChemistrySulfur-Based Synthesis Techniques

What the study found

The study reports a new way to make 2-quinolones, which are nitrogen-containing ring compounds, from (E)-2-aminocinnamic acid derivatives. The same general approach also works for making all regioisomers of 2-aza-quinolones from 2-amino-aza-cinnamate derivatives.

Why the authors say this matters

The authors state that the method has practical value because it uses simple operations, allows easy isolation of the quinolones by recrystallization, and can be scaled up to gram quantities. The findings suggest the protocol may be broadly useful for making these compounds.

What the researchers tested

The researchers tested thiolate-mediated cyclization of (E)-2-aminocinnamic acid derivatives. In their proposed sequence, the thiolate first adds to the starting material, forming β-sulfide-substituted dihydrocinnamic acid intermediates, which then cyclize intramolecularly and lose hydrogen sulfide to form the quinolone products.

What worked and what didn't

A broad range of 2-aminocinnamic acid derivatives was compatible with the transformation, and the corresponding 2-quinolones were obtained in excellent yields. The method was also applicable to 2-amino-aza-cinnamate derivatives for the synthesis of all regioisomers of 2-aza-quinolones. The abstract does not describe specific substrates that failed.

What to keep in mind

The available summary does not provide detailed limitations, side reactions, or substrate exclusions. It also does not give experimental conditions beyond the thiolate-mediated cyclization sequence and the noted scalability and isolation advantages.

Key points

  • A new thiolate-mediated protocol was developed for making 2-quinolones from (E)-2-aminocinnamic acid derivatives.
  • The proposed route involves thiolate addition, intramolecular condensation, and elimination of hydrogen sulfide.
  • A broad range of starting materials gave the corresponding 2-quinolones in excellent yields.
  • The method also worked for 2-amino-aza-cinnamate derivatives, producing all regioisomers of 2-aza-quinolones.
  • The authors note simple operation, recrystallization-based isolation, and gram-scale scalability.

Disclosure

Research title:
Thiolate-mediated cyclization yields 2-quinolones from aminocinnamic acids
Authors:
Tae Won Kim, Nuo Ming Goh, Cheol‐Hong Cheon
Institutions:
Korea University, Korea University, Korea University
Publication date:
2026-02-23
DOI:
10.1021/acsomega.5c13222
OpenAlex record:
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AI provenance: This post was generated by gpt-5.4-mini (OpenAI). The original authors did not write or review this post.