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
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).
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