A new DES-mediated synthesis of Henna-based benzopyranophenazines and benzoxanthenetriones

Abstract

AbstractMTPPBr/THFTCA-DES was prepared as a new deep eutectic solvent (DES) from a mixture (molar ratio 7:3) of methyltriphenyl-phosphonium bromide (MTPPBr) and tetrahydrofuran-2,3,4,5-tetra-carboxylic acid (THFTCA), and characterized with various spectroscopic techniques, densitometer, and eutectic point. Then, it was used as a new and powerful catalyst for the synthesis of two sets of biologically important compounds, namely the Henna-based benzopyranophenazines and benzoxan-thenetriones. Solvent-free conditions, short reaction time, high efficiency, and easy recycling and separation of the DES catalyst are among the most important features of the presented method. Also, there is a nice consistency between the proposed structure of the DES compound, the integration values of the 1H NMR peaks, and the ratio of MTPPBr to THFTCA obtained from the eutectic point phase diagram. In addition, the reduction of peak splitting patterns in DES compared to the two primary materials can be good evidence of the formation of hydrogen bonds between the two components.