ISONIAZID AS AN ALDEHDYE SCAVENGER: ANALYSIS OF ITS KINETICS, SELECTIVITY, AND PRACTICALITY IN PURIFYING ORGANIC REACTIONS

Abstract

Aurones are a member of the flavonoid family of natural products that have only been lightly investigated even though they possess interesting clinically relevant activity including anti-parasitic, anti-inflammatory, anti-fungal, anti-viral and anti-cancer. Preparation of aurones, most commonly through a Knovenagel condensation between an aryl aldehyde and a benzofuranone, while a simple one-step synthesis rarely yields a product of sufficient purity for assaying and thus require time consuming purifications. To expedite the synthesis of aurones, a method of purification utilizing Isoniazid as an aldehyde scavenger has been developed that allows for the rapid preparation of new collections of compounds in a matter of days, rather than the weeks that were required using conventional purification. Additionally, it is anticipated that this same scavenging approach can be applied to many other reactions of the aldehyde functional group, enabling convenient and rapid access to arrays generated by these reactions as well.