BF3·Et2O Catalysed 4-Aryl-3-phenyl-benzopyrones, Pro-SERMs, and Their Characterization

Area of Science:

• Organic Chemistry
• Medicinal Chemistry

Background:

• Selective Estrogen Receptor Modulators (SERMs) are crucial in treating various hormone-related conditions.
• Developing efficient synthetic routes for SERM precursors is essential for drug discovery and development.

Purpose of the Study:

• To synthesize a novel precursor for SERMs, 4-(4-hydroxy-benzyl)-3-phenyl-chromen-2-one.
• To establish efficient and selective synthetic methodologies for this precursor.

Main Methods:

• Two distinct synthetic methodologies were explored for the target compound.
• Catalysis screening using Lewis acids such as BF3·Et2O, AlCl3, FeCl3, and SnCl4 was performed.

Main Results:

• A novel compound, 4-(4-hydroxy-benzyl)-3-phenyl-chromen-2-one, was successfully synthesized.
• The anhydrous BF3·Et2O catalyzed reaction demonstrated high selectivity for the desired product.
• Alternative catalysts (AlCl3, FeCl3, SnCl4) resulted in nonselective reactions.

Conclusions:

• Anhydrous BF3·Et2O is an effective catalyst for the selective synthesis of the SERM precursor.
• The developed method offers a potentially shorter and higher-yielding route compared to existing methods.