Reactivity switch-over of 4-hydroxydithiocoumarins under various conditions and their application in organic synthesis
Md. Belal, Santa Mondal, Sabina Yashmin, Abu T. Khan
Abstract
4-Hydroxydithiocoumarin is a valuable organic precursor to architect important heterocycles. The three different reactive nucleophilic sites in 4-hydroxydithiocoumarins display intriguing regioselectivity in their reaction towards various electrophiles. Previously, 4-hydroxydithiocoumarins have been used in the synthesis of heterocycles using Claisen and thio-Claisen reactions. Hetero-Diels-Alder reactions involving 4-hydroxydithiocoumarins have proven to be very convenient in assembling complex molecular organic frameworks from readily available feedstocks. Development of multicomponent reactions employing 4-hydroxydithiocoumarins has given rise to several important reaction protocols to access polycyclic compounds. Recently, this moiety has been used in forging some unusual S-S, S-N and S-O bonds under oxidative conditions which further explores its hidden reactivity in organic synthesis. Besides that, hydrothiolation of various alkynes and alkenes using 4-hydroxydithiocoumarins has led to the synthesis of some potential lead molecules. This mini-review provides an account of the reactivity pattern of 4-hydroxydithiocoumarins and their strategic applications in various reactions for the synthesis of several heterocycles and other important organic syntheses.