Green synthesis of spiro[indoline-3,4\u2032-pyrano[2,3-c]pyrazoles] using Fe3O4@l-arginine as a robust and reusable catalyst

Mohammad Ali Ghasemzadeh,Boshra Mirhosseini-Eshkevari,Mohammad Hossein Abdollahi-Basir

doi:10.1186/s13065-019-0636-1

Mohammad Ali Ghasemzadeh, Boshra Mirhosseini-Eshkevari + Show 1 more

Open Access

https://doi.org/10.1186/s13065-019-0636-1

Copy DOI

Journal: BMC Chemistry	Publication Date: Oct 11, 2019
Citations: 15	License type: open-access

Affiliation: Qom Islamic Azad University, University of Guilan

Abstract

The synthesized Fe3O4@l-arginine showed strong catalytic performance in the one-pot synthesis of spiropyranopyrazoles via the reactions of hydrazines, β-keto esters, isatins, and malononitrile or ethyl cyanoacetate under solvent-free conditions. The biologically active heterocyclic compounds including spiropyranopyrazole derivatives were efficiently synthesized in short reaction times and excellent yields in the presence of Fe3O4/l-arginine at room temperature. The highlighted features of the Fe3O4@l-arginine nanocomposite are highly stable, easy to separate, low loading, cost-effective with easy preparation and reusability of the catalyst. The heterogeneous nanocomposite was fully characterized by SEM, EDX, FT-IR, XRD and TEM analysis.

Highlights

One-pot multi-component reactions (MCRs), is an interesting synthetic strategy for the synthesis of small-molecule libraries with various degrees of structural variety because various organic moieties are joined in one step for carbon–carbon and carbon-heteroatom bond formation [1, 2]
In continuation of our study in the synthesis of heterocyclic compounds using heterogeneous nanostructures [40,41,42,43,44], we describe a highly efficient and straightforward method for the synthesis of spiro[indoline-3,4′pyrano[2,3-c]pyrazoles] via multi-component reaction of hydrazines, β-keto esters, isatin and malononitrile or ethyl cyanoacetate using Fe3O4@l-arginine as a green, economic, available and environmentally benign nanocatalyst under solvent-free conditions (Fig. 1)
The earned lattice parameter of the nanoparticle Fe3O4@l-arginine using X-ray diffraction (XRD) technique coincided to the standard parameters of magnetite

Summary

Introduction

One-pot multi-component reactions (MCRs), is an interesting synthetic strategy for the synthesis of small-molecule libraries with various degrees of structural variety because various organic moieties are joined in one step for carbon–carbon and carbon-heteroatom bond formation [1, 2]. There are only two reported methods in the literature for the synthesis of spiro[indoline-3,4′pyrano[2,3-c]pyrazole] derivatives via four-component reaction of hydrazines, ethyl acetoacetate, isatins, and malononitrile or ethyl cyanoacetate which have been done in the presence of piperidine [19], and Et3N [20]. In continuation of our study in the synthesis of heterocyclic compounds using heterogeneous nanostructures [40,41,42,43,44], we describe a highly efficient and straightforward method for the synthesis of spiro[indoline-3,4′pyrano[2,3-c]pyrazoles] via multi-component reaction of hydrazines, β-keto esters, isatin and malononitrile or ethyl cyanoacetate using Fe3O4@l-arginine as a green, economic, available and environmentally benign nanocatalyst under solvent-free conditions (Fig. 1).

Results

Conclusion