Synthesis Chalones and Their Isomerization into Flavanones and Azaflavanones

Abstract

Flavanones [2-aryl-2,3-dihydrochromen-4(1H)ones] and 2-aryl-2,3-dihydroquinolin-4(1H)-ones are valuable precursors in the synthesis of important pharmacological scaffolds, so efficient methodologies towards their synthesis are important in the medicinal chemistry context. Their synthesis also involves theoretical concepts such as aldol condensation, isomerization, and catalysis that make it useful in an undergraduate organic chemistry laboratory. The use of both microwave irradiation as a source of energy to promote reactions and efficient catalysts are considered within green chemistry principles, mostly because the reaction yields are improved and reaction time decreased. In this paper, the efficiency of microwave irradiation use in the synthesis of chalcone derivatives and efficient catalyst systems to promote their isomerization into flavanones and 2-aryl-2,3-dihydroquinolin-4(1H)-ones is demonstrated.

Keywords

• flavanones
• 2-aryl-2,3-dihydroquinolin-4(1<i>H</i>)-ones
• chalcones
• microwaves
• proton sponge
• montmorillonite K10