A Domino Approach for the Synthesis of α,β‐Epoxy Ketones from Carbonyl Compounds under Neat Conditions at Ambient Temperature

Abstract

An efficient method has been developed for the synthesis of α,β‐epoxy ketones from one pot reaction between aldehydes and ketones in presence of cesium carbonate and tert‐butyl hydrogen peroxide (TBHP) under neat conditions. In this methodology we have used the one pot domino type reaction with aldehydes and ketones to get α,β‐epoxy ketones without presynthesized chalcone precursors. A library of α,β‐epoxy ketones having a variety of substituents has been synthesized. Clean reaction, mild reaction conditions, ease of product isolation/purification, easily accessible reactants, wide substrates scope and metal and solvent‐free and environmental friendly reaction conditions are the notable advantages of the present method. The present methodology is applicable to gram scale synthesis.

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

“…Metal and solvent free conditions have been reported in the synthesis of epoxy chalcones in the presence of TBHP and cesium carbonate with an excellent (96%) yield [53]. Green and ecofriendly alkaloid Cinchona is natural catalyst derived from Cinchona plants of Rubiaceae family, having structural activity that already illustrated by Jew and Park [61].…”

“…Epoxy chalcone has been prepared via consecutive reaction of acetophenone and aldehyde via Claisen Schmidt condensation followed by epoxidation using various oxidizing reagent such as trichloroisocyanuric acid (TCCA) and chiral quaternary ammonium salt i.e. Cinchona alkaloid [49], poly(amino acid) [50], poly-l-leucine immobilized [51], bifunctional nanocrystalline MgO [52] and TBHP/Cs 2 CO 3 [53], H 2 O 2 [54][55][56] (route v). Claisen Schmidt condensation is a common and facile method in the synthesis of chalcone derivatives [57].…”