Pyridone and quinolinone skeletons are widely found in natural products and drug molecules, such as the antibiotic drug molecule Diazaquinomycin B and the natural product Benzosimuline with anti-platelet aggregation activity. The efficient and highly selective synthesis of this kind of skeleton has important application prospects.
Figure 1 Natural products and drug molecules containing pyridone and quinolinone structural units
Professor Zhou Qianghui of Wuhan University conducted research on the Catellani reaction of non-aromatic systems. For the first time, iodopyridone compounds were used as substrates to participate in the Catellani reaction, and aryl bromides and alkyl bromides were used as electrophiles respectively to achieve this type of reaction. Arylation and alkylation reactions at the C3 and C5 positions of alkenyl iodides can efficiently synthesize a series of pyridone and quinolinone derivatives. This reaction is completed under the synergistic catalysis of palladium acetate and C2-substituted NBE derivatives, and does not require the addition of additional phosphine ligands. This reaction has the advantages of cheap and easily available raw materials, mild reaction conditions, good chemical selectivity, and wide substrate application range (there are 33 examples in the arylation system, with a yield as high as 93%; there are 41 examples in the alkylation system, and the product rate as high as 96%) and other advantages. Moreover, in the alkylation system, when deuterated methyl p-toluenesulfonate is used as the alkylation reagent, deuterated methyl labeled products can be easily obtained. These research advances are expected to be used in related medicinal chemistry and natural product synthesis. get applied.
Figure 2 Non-aromatic system type substrates involved in Catellani reaction
Zhou Qianghui, professor and doctoral supervisor, graduated from the School of Chemistry and Molecular Engineering of Peking University in 2005 with a bachelor's degree. His supervisors were Professor Wu Jinguang and Associate Professor Li Weihong. He graduated from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences in 2010 with a doctorate in science. His supervisor was Professor Ma Dawei; from 2011 to 2015, he engaged in postdoctoral research at Scripps Research Institute in the United States, and his co-supervisor was Professor Phil S. Baran. From 2015 to present, he serves as a professor at the School of Chemistry and Molecular Sciences of Wuhan University. Professor Zhou Qianghui has been committed to the efficient total synthesis of bioactive molecules, green drug process development, goal-oriented and structural diversity-oriented innovative synthesis methodology research, and related cross-research in chemical biology and medicinal chemistry. Professor Zhou Qianghui was funded by the National Natural Science Foundation of China's Outstanding Youth Science Fund Project, and has won the Outstanding Youth (Faculty) of Wuhan University (2023), the WuXi AppTec Life Chemistry Research Award (2022), and the Hubei Province Chemistry and Chemical Engineering Youth Innovation Award (2019) and Thieme Chemistry Journals Award (2017), and was selected into the National High-Level Talent Youth Project (2015). In terms of academic part-time work, he serves as the deputy secretary-general of the Process Chemistry Committee of the Chinese Chemical Society and a young editorial board member of Science of Synthesis, Green Synth. Catal. and "Organic Chemistry".
Bailingwei exclusively supplies a series of pyridone heterocyclic compounds developed by Professor Zhou Qianghui of Wuhan University, with high purity and diverse structures, which facilitates research in the field of medicinal chemistry!
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向阳 翟
