Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters

摘要

Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.