3-Methyl-1-Sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature

Abstract

New Brønsted acidic ionic liquid, 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} was used as an efficient, green and reusable catalyst and solvent for the synthesis of N-sulfonyl imines via the condensation of sulfonamides with aldehydes as well as isatin. The reactions proceeded at room temperature and the title compounds were obtained in high to excellent yields and in relatively short reaction times.

Multicomponent Reactions in Ionic Liquids

“…[ Brønsted acidic ionic liquids have designed to replace solid acids and traditional mineral liquid acids like sulfuric acid and hydrochloric acid in chemical procedures. [65], [66] Fang et al's dicationic acidic IL catalytic approach, in what amounted to a modified Biginelli approach, resulted in the synthesis of 3,4-dihydropyrimidin-2(1H)-one and 3,4-dihydropyrimidin-2(1H)-thione derivatives (Scheme 21), in good yields. [68] The products could be separated simply from the catalyst-water system, and the catalysts could be reused at least six times without noticeably reducing catalytic activity.…”

Design, characterization and application of silica-bonded imidazolium-sulfonic acid chloride as a novel, active and efficient nanostructured catalyst in the synthesis of hexahydroquinolines

“…In this work, in continuation of our previous studies on the preparation and applications of acidic ILs and solid salts in organic transformations [30][31][32][33][34][35][36][37][38][39][40][41][42], and also previous works on the synthesis of silica-bonded imidazolium compounds [43][44][45][46], we have synthesized silica-bonded imidazolium-sulfonic acid chloride (SBISAC) (Figure 1) in which SAFIS have been immobilized on silica gel, and characterized it by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), scanning electron microscope (SEM), transmission electron microscopy (TEM) and energy dispersive X-ray analysis (EDX). Then, we have utilized SBISAC as a highly efficient, stable, reusable and heterogeneous nanocatalyst for the preparation of hexahydroquinolines at 50 °C under solvent-free conditions (Scheme 1).…”

“…Recently, we introduced a new category of acidic ionic liquids (ILs) and solid salts, namely sulfonic acid-functionalized imidazolium salts (SAFIS) which published in this journal [30], and applied them as organocatalysts or organoreagents for preparation of 1-amidoalkyl-2-naphthols [30], N-sulfonyl imines [31], nitro aromatic compounds [32,33], bis(indolyl)methans [34], benzimidazoles [35], xanthenes [36], 1-carbamatoalkyl-2-naphthols [37], 4,4'-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s [38], t-butyl aryl carbamates [39], 1,2,4,5-tetrasubstituted imidazoles [40], β-acetamido ketones [41], and hexahydroquinolines [42].…”

Silica-bonded 1,4-diaza-bicyclo[2.2.2]octane-sulfonic acid chloride catalyzed synthesis of spiropyran derivatives

“…Recently, we have prepared a new category of ionic liquids and solid salts (with an organic cation), namely sulfonic acid functionalized imidazolium salts (SAFIS) [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]. In this class of salts, S-N bond formation in imidazole ring, as five member's heterocyclic compounds, was reported for the first time.…”