Recently, multi-component, one-pot reactions have been shown to be efficient and environmentally friendly methods compared to traditional, linear-step syntheses. Heterogeneous catalyzed ...multicomponent reactions are one of the green approaches to the synthesis of organic compounds, especially pyrazoles and their derivatives. Here we demonstrate the one-pot synthesis of pyrazoles using heterogeneous nickel-based catalysts for the condensation of various hydrazine, ketone derivatives, and aldehyde derivatives at room temperature. The thus synthesized heterogeneous catalyst can be reused up to the seventh cycle without much loss of catalytic activity.
A simple and efficient method for the synthesis of spirooxindole derivatives via a three-component reaction of isatin, 5-aminopyrazole, and 1,3-dicarbonylcompounds (or β-oxo-benzenepropanenitrile) ...catalyzed by copper triflate in ethanol is described. The advantages of this method include high efficiency, mild reaction conditions, recoverable catalyst, and environmentally benign conditions.
Described herein is a facile and efficient methodology for diversity-oriented one-pot multicomponent synthesis of 3-aminomethyl quaternary carbon oxindole fused five-membered carbocyclic ...spirooxindoles 5via knoevenagel condensation/Michael/cyclization and then aminomethylation reaction. A wide variety of products with varying degrees of substitution around it, were obtained smoothly with high efficiency (up to overall yield 73% and >20:1 diastereoselectivity). In particular, their biological activities against these three cell lines K562, A549 and PC-3 have been evaluated. These results suggested that most of 3-aminomethyl quaternary carbon oxindole fused five-membered carbocyclic spirooxindoles 5 showed equipotent or more potent than the positive control of Cisplatin (up to 3.4 times).
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•A methodology for synthesis of spirooxindole derivatives was developed.•Products were obtained smoothly with high efficiency.•Promising activities against three human cancer cell lines have been demonstrated.
The study introduces a groundbreaking continuous system that combines an extruder and grinder to enable catalyst-free and solvent-free reactions under mild conditions. This temperature-controlled ...system facilitates the synthesis of highly functionalized chromenes, which have valuable applications in generating combinatorial libraries and complex target molecules. The newly developed mill extruder machine offers several advantages for industrial production on a large scale. It effectively reduces waste, saves energy, and enhances time efficiency. This system represents a significant advancement in the field, providing a new strategy for one-pot synthesis of various types of highly functionalized spirooxindoles and chromenes. Remarkably, these reactions can be accomplished within a short timeframe of 2-10 min, yielding impressive results of 75-98%. The results demonstrate superior performance compared to traditional reaction methods, making it an appealing tool and hotspot area of research in green chemistry.
A series of hydrotalcite/hydroxyapatite composites were investigated as novel catalysts in the green synthesis of chromenes in high conversions (up to 78% after 2 h), under solvent-free and mild ...conditions, from salycilaldehydes and cyano compounds. Materials were prepared by three different methods: impregnation of hydroxyapatite over hydrotalcite already crystallized; impregnation of hydrotalcite over hydroxyapatite and crystallization of both the components simultaneously. The composites resulted in the materials with high activity and selectivity for the 2-amino-4H-chromene synthesis. The catalytic performance was depending on the catalyst synthesis method and governed by the basicity of the samples and textural properties also varying as a function of the used cyano compound. Observed reactivity was attributed to the high dispersion of the hydrotalcite particles on the hydroxyapatite component, resulting in a considerable increase of the surface areas from 3 to 154 m2/g, and thus, given rising to a high concentration of superficial hydroxyls reaching 7.1 × 1014 sites/g catalyst. Broad pore size distributions in composites enabled a rapid diffusion of the reactants to reach the basic hydroxyl sites.
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•A new family of hydrotalcite/hydroxyapatite (HT/HA) composites were synthesized.•They were successfully applied as catalysts in the chromene synthesis.•The sizes of HT particles in the composites depend on the synthesis method.•High dispersion of HT particles increases the number of basic sites and surface area.•HT/HA composites are cheap, non-toxic and efficient catalysts.
•Design and preparation of inexpensive, reusable and highly efficient solid base catalyst.•Green synthesis of pyrazolophthalazines using perlite NPs/SiO2/guanidine.•High to excellent yield of ...products.
In this study 1H-pyrazolo 1,2-b phthalazine-5,10-diones was prepared via the four-component condensation of phethalimide, hydrazine hydrate, malononitrile (or ethylcyanoacetate) and aldehyde derivatives in the presence of modified perlite nanoparticles (perlite NPs/SiO2/guanidine) as a natural, inexpensive, effective and heterogeneous catalyst. Solid base catalyst was prepared through a three steps process and characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM), X-ray diffraction (XRD) and energy-dispersive X-ray spectroscopy (EDX) and themogravimetric (TGA) analyses. Green reaction conditions, high to excellent yield of products after short reaction times, easy workup and clean and eco-friendly procedure are some advantageous of presented method.
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An efficient and eco-friendly method for the synthesis of spirooxindoles with fused tetrahydrochromenes has been demonstrated using basic nanocrystalline MgO catalyst in aqueous condition. The method ...has been applied for the synthesis of a range of compounds with variable functionalities in excellent yield and selectivity.
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•Template effects in multicomponent polynuclear coordination compounds are reviewed.•Combinations of simple templates produce sophisticated architectures.•Focus on halide-templated ...coordination complexes.•Physicochemical properties controlled by combinations of multiple templates.
This account covers template effects that lead to the formation of polynuclear coordination compounds, with a focus on how the interplay of the structure-directing effects of multiple agents (including inorganic anions and organic ligands) combine to influence the geometry and nuclearity of metal-containing assemblies. Simple anions and ligands impart defined geometric shapes (triangles, squares, hexagons) onto oligonuclear assemblies, and these shapes can combine to produce a range of more sophisticated metallo-supramolecular architectures (including Platonic and Archimedean solids). An understanding of the structure-directing effects of simple templates is therefore necessary to predict or rationalise such polynuclear architectures, which may have wide-ranging applications in catalysis, in magnetism, as sensors, etc. This article primarily focuses on halide-templated assemblies of first row transition metal ions (particularly manganese coordination clusters and vanadates), but the principles discussed herein are applicable to a much wider range of coordination compounds.
Investigating novel compounds that may be useful in designing new, less toxic, selective, and potent breast anticancer agents is still the main challenge for medicinal chemists. Thus, in the present ...work, acetylthiophene was used as a building block to synthesize a novel series of thiazole-bearing thiophene derivatives. The structures of the synthesized compounds were elucidated based on elemental analysis and spectral measurements. The cytotoxic activities of the synthesized compounds were evaluated against MCF-7 tumor cells and compared to a cisplatin reference drug, and against the LLC-Mk2 normal cell line using the MTT assay, and the results revealed promising activities for compounds 4b and 13a. The active compounds were subjected to molecular modeling using MOE 2019, the pharmacokinetics were studied using SwissADME, and a toxicity radar was obtained from the biological screening data. The results obtained from the computational studies supported the results obtained from the anticancer biological studies.
We report efficient synthetic methodologies for the preparation of 3-amino and 3-hydroxy 3-pyrrolin-2-ones (unsaturated γ-lactams) through a multicomponent reaction of amines, aldehydes and acetylene ...or pyruvate derivatives. The densely substituted γ-lactam substrates show in vitro cytotoxicity, inhibiting the growth of the carcinoma human tumor cell lines RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma) and A549 (carcinomic human alveolar basal epithelial cell). In view of the possibilities for the diversity of the substituents that offer a multicomponent, synthetic methodology, an extensive structure-activity profile is presented. In addition, the bioisosteric replacement of the flat ester group by a tetrahedral phosphonate or phosphine oxide moiety in γ-lactam substrates leads to increased growth inhibition activity. Cell morphology analysis and flow cytometry assays indicate that the main pathway by which our compounds induce cytotoxicity is based on the activation of the intracellular apoptotic mechanism.
