ZnO nanoparticles supported on dendritic fibrous nanosilica as efficient catalysts for the one-pot synthesis of quinazoline-2,4(1H,3H)-diones.

Farzaneh Shamsa,Malihe Sadat Hosseiny,Jamshid Mehrzad,Rahele Zhiani,Alireza Motavalizadehkakhky

doi:10.1039/d1ra07197a

Farzaneh Shamsa, Malihe Sadat Hosseiny + Show 3 more

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https://doi.org/10.1039/d1ra07197a

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Abstract

The transmutation of waste into valuable materials has a special place in green chemistry. Herein, we report the preparation of quinazoline-2,4(1H,3H)-diones from 2-iodoaniline, isocyanides, and carbon dioxide in the presence of ZnO NPs stably placed on the surface of dendritic fibrous nanosilica by cellulose (DFNS/cellulose-ZnO) as a catalyst. This is a great economic strategy to create three bonds in a one-pot multicomponent reaction step employing functional groups. To prepare the catalyst, the dendritic fibrous nanosilica surface was first activated using cellulose as a substrate to support ZnO NPs. Cellulose acts as a stabilizing and reducing agent for the ZnO nanocatalyst and eliminates the need for a reducing agent. The structure of the prepared DFNS/cellulose-ZnO was examined by various methods, including thermogravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and inductively coupled plasma (ICP). The largest amount of quinazoline-2,4(1H,3H)-diones was obtained under ideal situations in the presence of 5 mg of DFNS/cellulose-ZnO under carbon dioxide (1 atm) utilizing a balloon set at 70 °C for 3 hours. The substance was reused for ten consecutive runs and the quinazoline-2,4(1H,3H)-dione content was more than 92% each time. This indicates the potential for application in the green and economic production of quinazoline-2,4(1H,3H)-diones, especially from low-cost feedstocks.

Highlights

Scienti c circles have shown great interest in the employment of non-venomous, recyclable, available, and costeffective CO2 to produce valuable organic composites.[1,2,3,4] Remarkable progress has been made in the area, mostly by dblock metal-catalyzed reactions
We report the preparation of quinazoline-2,4(1H,3H)-diones from 2-iodoaniline, isocyanides, and carbon dioxide in the presence of ZnO NPs stably placed on the surface of dendritic fibrous nanosilica by cellulose (DFNS/ cellulose-ZnO) as a catalyst
The structure of the prepared DFNS/cellulose-ZnO was examined by various methods, including thermogravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and inductively coupled plasma (ICP)

Summary

Introduction

Scienti c circles have shown great interest in the employment of non-venomous, recyclable, available, and costeffective CO2 to produce valuable organic composites.[1,2,3,4] Remarkable progress has been made in the area, mostly by dblock metal-catalyzed reactions. Isocyanides have been mainly employed as signi cant synthons in modern synthetic organic chemistry, especially for N-containing heterocyclic composite synthesis through chemical transformations like multi-component reactions.[12,13,14,15,16,17,18,19,20,21,22] Today, different transition metal (such as Cu,[24] Pd, Ni,[27] Ag, and Co26)-catalyzed. Combining isocyanide and CO2 through a multi-element reaction to produce N3-substituted 2,4(1H,3H)-quinazolinediones may seem like an interesting approach. In the presence of transition metal catalysts, this sort of multi-element reaction is yet underdeveloped.[34] The reason is that the solubility of carbon dioxide in organic solvents is very low, and this low solubility is reduced with increasing temperature. Combining CO2 and isocyanides in a multi-element reaction is not easy

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