One-pot sequential reaction to 2-substituted-phenanthridinones from N-methoxybenzamides

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Phenanthridinones are important heterocyclic compounds with diverse biological activities.
• Efficient synthetic routes for substituted phenanthridinones are crucial for medicinal chemistry and drug discovery.

Purpose of the Study:

• To develop a novel, efficient, and one-pot method for synthesizing 2-substituted phenanthridinones.
• To utilize sequential C-H functionalization reactions for constructing the phenanthridinone core.

Main Methods:

• Employing a hypervalent iodine reagent for sequential amidation of arenes and regioselective halogenation.
• Conducting the synthesis in a one-pot manner at room temperature.

Main Results:

• Successful synthesis of 2-bromo/chloro-phenanthridinones with good to high yields.
• Demonstrated efficiency in constructing various 2-substituted phenanthridinones.
• Concise synthesis of the natural product PJ34 using the developed method.

Conclusions:

• The developed method provides an efficient and versatile route to 2-substituted phenanthridinones.
• The one-pot sequential C-H functionalization strategy is effective for complex molecule synthesis.
• This methodology offers a valuable tool for accessing phenanthridinone derivatives.