Synthesis of Novel Imidazolium and Benzimidazolium Salts from Halomethyl Derivatives of 4-Pyrones

Abstract

A series of mono-and bis-benzimidazolium and imidazolium salts of 4-pyrone derivatives has been synthesized in good yields, by various quaternization reactions of halomethyl derivatives of 4H-pyran-4-ones. These salts can be used as novel precursors of functionalized N-heterocyclic carbenes and some of them as novel ionic liquids.

Kojic acid in organic synthesis

“…Ghasemi et al 163 reported a series of imidazolium and benzimidazolium salts of KA derivatives 284 and 285, which were used to synthesize functionalized N -heterocyclic carbenes and ionic liquids. Treatment of chloromethyl KA derivatives with N -methylimidazole in CH 3 CN at 25 • C for 24 h or N -alkylbenzimidazoles in the presence of KI at 70 • C for 10 h afforded imidazolium salts 284a or benzimidazolium salts 285 in 83%-88% or 68%-90% yields, respectively.…”

Base-Mediated N- and O-Arylations of NH-Containing Heterocycles, Heterocyclic Amines and Phenols

“…Diaryl ethers and N-aryl azoles which are accessible through the above methodologies, have emerged as important classes of organic compounds with extensive applications in chemical, pharmaceutical, life sciences and polymer industries. [23][24][25][26] Through our interest in the synthesis of polyaromatic heterocyclic frameworks, [27][28] we now report the base-mediated O-arylation of some phenolic compounds for preparing unsymmetrical diaryl ethers most of which contain a heterocyclic motif, and also N-arylation of NH-containing heterocycles and some heterocyclic amines. Both classes of the reactions were carried out using active aryl halides with electron-withdrawing groups.…”