Efficient Synthesis of Pyridone and Quinolinone Skeletons for Medicinal Chemistry

Pyridone and quinolinone skeletons are essential components in numerous natural products and drug molecules. Examples include the antibiotic Diazaquinomycin B and Benzosimuline, a natural product with anti-platelet aggregation activity. The efficient and selective synthesis of these skeletons holds immense potential for applications in medicinal chemistry and natural product synthesis.

Natural products and drug molecules containing pyridone and quinolinone structural units

Figure 1 Natural products and drug molecules containing pyridone and quinolinone structural units

 

Innovative Research by Professor Zhou Qianghui

Professor Zhou Qianghui of Wuhan University has made groundbreaking progress in the field of Catellani reactions applied to non-aromatic systems. His research introduces iodopyridone compounds as substrates in Catellani reactions, using aryl bromides and alkyl bromides as electrophiles. This method enables efficient C3 and C5 arylation and alkylation of alkenyl iodides, synthesizing a variety of pyridone and quinolinone derivatives.

Key Features of the Reaction:

  1. Catalysis: Achieved through the synergistic effects of palladium acetate and C2-substituted NBE derivatives.
  2. Phosphine-Free: No additional phosphine ligands are required.
  3. Cost-Efficiency: Uses affordable and readily available raw materials.
  4. Mild Reaction Conditions: Suitable for a wide range of substrates.
  5. High Yields:
    • Arylation system: 33 examples with yields up to 93%.
    • Alkylation system: 41 examples with yields up to 96%.
  6. Deuterated Methyl Labeling: Deuterated methyl-labeled products can be conveniently synthesized using deuterated methyl p-toluenesulfonate.

These advancements pave the way for significant applications in medicinal chemistry, enabling the efficient synthesis of natural product analogs and new drug molecules.

Non-aromatic system type substrates involved in Catellani reaction
Figure 2 Non-aromatic system type substrates involved in Catellani reaction
 
Professor Zhou Qianghui of Wuhan University has made groundbreaking progress in the field of Catellani reactions applied to non-aromatic systems

About Professor Zhou Qianghui

Bachelor’s degree from Peking University (2005), under the mentorship of Professors Wu Jinguang and Li Weihong.

Ph.D. from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (2010), supervised by Professor Ma Dawei.
Postdoctoral research at the Scripps Research Institute, USA (2011–2015), under Professor Phil S. Baran.

 

 

Current Role:

  • Professor at Wuhan University’s School of Chemistry and Molecular Sciences.
  • Research focuses on bioactive molecule synthesis, green drug processes, and innovative methodologies in chemical biology and medicinal chemistry.

Achievements:

  • Funded by the National Natural Science Foundation of China's Outstanding Youth Science Fund Project.
  • Recipient of awards such as the WuXi AppTec Life Chemistry Research Award (2022), Thieme Chemistry Journals Award (2017), and more.
  • Holds roles such as Deputy Secretary-General of the Process Chemistry Committee of the Chinese Chemical Society.

J&K Scientific: Exclusive Supplier of Pyridone Heterocycles

J&K Scientific proudly supplies a series of pyridone heterocyclic compounds developed by Professor Zhou Qianghui. These compounds, characterized by high purity and structural diversity, are instrumental for research in medicinal chemistry and beyond.

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By 向阳 翟

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