Simple and Efficient One Step Synthesis of Functionalized Flavanones and Chalcones

Abstract

A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.

Microwave-Assisted Synthesis of Potent Antimicrobial Agents of Flavanone Derivatives

“…The starting flavanone derivatives 4a-d were prepared from the corresponding 2'-hydroxyacetophenones according to the literature method 14 . The synthesis of phenylhydrazone derivatives 5a-d was attempted by the reaction of flavanone 4a-d with phenylhydrazine under microwave irradiation in the presence of 1 ml of acetic acid, which resulted in good to excellent yield of pure phenylhydrazone products in very short reaction times (1-2 min.).…”

“…Recently, we reported the simple and efficient microwave-assisted synthesis of 2'-hydroxychalcones and flavanones in one step with high yield and no side products 14 highlighting the role of different substituent in directing the reaction to pure chalcone or flavanone product ( Figure 1). …”

“…Microwave experiments were carried out using CEM MARS synthator TM microwave apparatus with temperature control for MW experiments using IR sensor. Flavanone 4a-d 14 was prepared according to the reported literature.…”

“…reaction of o-hydroxyacetophenones 1 with benzaldehydes 2 to produce chalcone intermediates 3 using various catalysts [10][11][12][13][14] , followed by cyclization with various bases 15 , acids 16 , or other materials (Scheme 1) 17 .…”

Tetrahydronaphthalene as a precursor of new series of chalcones, flavanones, and flavone

“…20 Recently, Chen 18 and co-workers described an environmentally friendly method using tertiary amines as bases in water or ethanol as solvents, directly affording the desired flavanones.…”