Magnetic chitosan stabilized Cu(II)-tetrazole complex: an effective nanocatalyst for the synthesis of 3-imino-2-phenylisoindolin-1-one derivatives under ultrasound irradiation

Abstract

In the present research, a recyclable catalyst has been prepared via a simple approach using chitosan as a linear polysaccharide. This paper reports the synthesis of novel copper(II) complex of 5-phenyl-1H-tetrazole immobilized on magnetic chitosan (MCS@PhTet@Cu(II)) as an effective catalyst. Transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), vibrating sample magnetometer (VSM), Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), and inductively coupled plasma mass spectrometry (ICP-MS) techniques were applied for the characterization of the catalyst. The catalytic activity of MCS@PhTet@Cu(II) was evaluated in the ultrasound-assisted synthesis of 3-imino-2-phenylisoindolin-1-one derivatives via the reaction between benzoyl chloride and arylcyanamides in ethanol at ambient temperature. Utilizing a wide variety of arylcyanamides under mild conditions, no use of toxic organic solvents, moderate reaction time, high yields along with catalyst excellent reusability and easy separation of the products without any tedious separation techniques, made this method a novel and simple process. The resulting heterogeneous catalyst showed valuable advantages such as easier work-up, better stability, and greater separation ability using an external magnet. The catalyst showed high efficacy and recyclability even after five cycles with no significant loss of its efficacy. The present methodology provides a path for the preparation of structurally diverse heterocyclic compounds, which may exhibit important biological activity.

Magnetic NH2-MIL-101(Al)/Chitosan nanocomposite as a novel adsorbent for the removal of azithromycin: modeling and process optimization

“…Although MOFs-based adsorbents provide some advantages, however, their tendency to aggregate and lose during the recovery process is considered a respective drawback for their applications 23 . Chitosan (Cs) is a natural, non-toxic, and inexpensive polysaccharide that with its unique physical and chemical properties including biocompatibility, biodegradability, flexibility, and various functional groups 24 , has been proposed as a substrate to prevent MOF agglomeration/aggregation in the present study. Furthermore, the presence of free hydroxyl and amino groups in chitosan structure and permission of their chemical modification can facilitate the adsorption of various types of pollutants in chitosan-derived nanocomposites 25 .…”

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

“…Nasrollahzadeh et al reported a synthetic procedure to access 3-imino-2-phenylisoindolin-1-one derivatives (58) using magnetic nanocatalysts, chitosan stabilised Cu(II)tetrazole complex (MCS@PhTet@Cu(II)) under ultrasoundirradiation from substituted phenylcyanamides (56) and benzoyl chloride (57) in ethanol at room temperature (Scheme 14). 68 The catalysts were obtained by coating Fe 3 O 4 NPs with chitosan followed by O-silylation using (3-chloropropyl)trimethoxysilane coupled with 5-phenyltetrazole and complexation using cupric chloride. The fully characterised catalysts were recycled in up to five catalytic runs with high efficacy, stability, and recyclability under external magnetism.…”