Synthesis of the first nanomagnetic particles with semicarbazide‐based acidic ionic liquid tag: an efficient catalyst for the synthesis of 3,3′‐(arylmethylene)bis(4‐hydroxycoumarin) and 1‐carbamato‐alkyl‐2‐naphthol derivatives under mild and green conditions

Abstract

Semicarbazide functionalized with chlorosulfonic acid on the surface of silica‐coated magnetic nanoparticles, {Fe3O4@SiO2@(CH2)3Semicarbazide‐SO3H/HCl}, as a novel magnetic Brønsted acid catalyst according to the aims of green chemistry was synthesized and fully characterized using Fourier transform infrared, UV–visible and energy‐dispersive X‐ray spectroscopies, X‐ray diffraction, scanning electron, transmission electron and atomic force microscopies and thermogravimetric analysis. The capability and excellent activity of this nanoparticle catalyst were exhibited in the synthesis of two series of compounds with important biological activities, namely 3,3′‐(arylmethylene)bis(4‐hydroxycoumarin) and 1‐carbamato‐alkyl‐2‐naphthol derivatives, under mild, green and solvent‐free conditions. To the best of our knowledge, this is the first study of the synthesis and application of {Fe3O4@SiO2@(CH2)3Semicarbazide‐SO3H/HCl} as Brønsted acid solid magnetic nanoparticles. Consequently the present study can open up a novel and promising intuition in the sequence of logical design, synthesis and applications of task‐specific Brønsted acid magnetic nanoparticle catalyst with favourable properties as a full‐fledged efficient material for sustainable approaches. Copyright © 2016 John Wiley & Sons, Ltd.

Application of a biological‐based nanomagnetic catalyst in the synthesis of bis‐pyrazols and pyrano[3,2‐c]pyrazoles

“…Usual heterogeneous nanomagnetic solid acid catalysts are hybrids of organic and inorganic materials with suitable tags. Solid acid catalysts should have a great many pores, many active acidic sites, high stability with good selectivity, recyclability and reusability, high turnover number and turnover frquency and also should be economically and environmentally sustainable . In this regard, we decided to apply a new biological‐based nanomagnetic solid acid with sulfonic acid tag, namely {Fe 3 O 4 @SiO 2 @(CH 2 ) 3 ‐thiourea dioxide‐SO 3 H/HCl}, in the synthesis of 4,4′‐(arylmethylene)bis(1 H –pyrazol‐5‐ol) derivatives and pyrano[3,2‐ c ]pyrazoles under mild and solvent‐free conditions (Scheme ).…”

Facile Synthesis of Bis‐Coumarins Using [BCMIM][Cl] Zwitter Ionic Liquid and Their Binding with Bovine Serum Albumin

“…Bis‐coumarin synthesis involves a Knoevenagel‐Michael addition, which is vital for generating C−C bonds in synthetic organic chemistry. A detailed review of the literature discloses the utilisation of numerous catalysts such as viologen‐based ionic porous organic polymer, [13] Amberlyst 15, [14] nanocatalysts, [15] Mohr's Salt, [16] ionic liquids, [15c,17] Aegle marmelos fruit ash, [18] carbon‐based acid catalyst, [2a] thiamine hydrochloride, [19] biosurfactants, [20] Meglumine, [21] trityl bromide, [22] Phosphotungstic acids, [23] melamine, [24] deep eutectic solvents (DES), [25] choline hydroxide, [26] and so on for the synthesis of biscoumarin. Although most of the stated methods are useful, yet holds several drawbacks, such as critical reaction conditions, expensive catalyst preparation process, low yields, longer reaction durations, and complex work‐up procedures.…”

L‐lysine‐Pd Complex Supported on Fe3O4MNPs: a novel recoverable magnetic nanocatalyst for Suzuki C‐C Cross‐Coupling reaction

“…high magnetic permeability, large specific surface area, small size, low cost and good stability. [ 65–69 ] The development of hybrid inorganic–organic nanocomposite catalyst has gained considerable attention due to its process ability, multi‐functionality, and the potential large‐scale production. [ 70–72 ] Immobilization of the homogeneous catalysts on these nanocomposites as a solid support will aid the recovery of the catalyst and minimizing the pollution via simple magnetic decantation.…”