Diastereoselective Synthesis of Functionalised Trans-Tetrahydrobenzofuran-4-Ones in an Aqueous Medium by using DABCO as an Efficient Catalyst

Abstract

A one-pot, efficient synthesis of 11 novel 2,3-diacylated trans-tetrahydrobenzofuran-4-one derivatives has been achieved via a three-component condensation of a N-(4-halophenacyl)-pyridinium bromide, a cyclic 1,3-diketone such as 5,5-dimethyl-1,3-cyclohexanedione (dimedone) or cyclohexane-1,3-dione and an arylglyoxal in the presence of catalytic amounts of 1,4-diaza-bicyclo[2.2.2]octane (DABCO) in water under reflux conditions. The attractive features of the method are excellent yields and high purity, short reaction times, easy work-up, and use of an inexpensive and non-toxic catalyst.