A potential DES catalyst for the fast and green synthesis of benzochromenopyrimidines and pyranopyrimidines

Abstract

Abstract A gentisic acid based-Deep Eutectic Solvent (MTPPBr/GA-DES) was synthesized by mixing one mole of methyl triphenylphosphonium bromide (MTPPBr) and one mole of gentisic acid (GA: 2,5-dihydroxy-benzoic acid) based on the eutectic point phase diagram. Then, it was characterized by FT-IR, NMR, densitometer, and TGA/DTA techniques and used as a potent and novel catalyst for the fast and green synthesis of: (i) Five new 2(a-e) and five known 2(f-j) benzo[6,7]chromeno[2,3-d]pyrimidines and (ii) One new (3a) and eleven known 3(b-l) pyrano[2,3-d]pyrimidines, in solvent-free conditions, short reaction times, and high yields. It is important to mention that for the synthesis of 2(a-j), there is only one reference which states that the reaction times are extremely long (720–2400 min), while these times are reduced to approximately 35–50 min in our proposed strategy, indicatinging that the rate of reactions will be 20–48 times faster, which is the clear and most obvious advantage of our approach.

Keywords

• Gentisic acid
• Deep eutectic solvent
• Green synthesis
• benzo[6,7]chromeno[2,3-d]pyrimidines
• pyrano[2,3-d]pyrimidines