Ultrasound-assisted and Efficient Knoevenagel Condensation Reaction Catalyzed by Silica Sodium Carbonate Nanoparticles

Abstract

An efficient and ultrasound-assisted route to the synthesis of arylidene malononitriles/methylciano-or ethylciano acetates in a onepot reaction catalyzed by silica sodium carbonate nanoparticles (SSC NPs) is described. In this reaction, SSC NPs demonstrated high efficiency as catalyst to obtain target products. By this achievement, a wide range of α,β-unsaturated compounds as Knoevenagel condensation products with good to excellent yields are obtained from reaction between numerous arylaldehydes, and malononitrile, methyl cianoacetate or ethyl cianoacetate. Target products which prepared in high yield and high purity can be candidate as important biologically active molecules. This method is an easy, cheap, rapid and highly efficient for the synthesis of desired products. In addition, capability of catalyst to separate from reaction mixture and reuse in further runs and being compatible with green chemistry are considered as other advantages of this procedure. All products were deduced from their FT-IR and FT-NMR spectroscopic and elemental analysis data.

Synthesis and identification of meta-(4-bromobenzyloxy) benzaldehyde thiosemicarbazone (MBBOTSC) as novel ligand for cadmium extraction by ultrasound assisted-dispersive-ionic liquid-liquid micro extraction method

“…Synthesis of TSC is performed in different ways: a) it is a two-step pathway in which hydrazine reacts with isothiocyanate and the product with aldehyde or ketone, which leads to TSCs [9], b) it is the opposite of pathway a, ie hydrazine first reacts with aldehydes or ketones and then the resulting compound reacts with isothiocyanate [10], c) it is a 4-step process, in which hydrazine first reacts with carbon disulfide and the resulting intermediate reacts with methyl iodide to form methylhydrazine thiocarbamate, eventually nucleophilic substitution with amines and a condensation reaction with an aldehyde or ketone produces TSC [11]. In continuation of our research on the synthesis of various compounds [12][13][14][15] and recent report introducing penicillamine as a metal chelator [16], herein, MBBOTSC as ligand containing sulfur and nitrogen has proposed as cadmium chelator.…”

Hantzsch‐like reaction of isoquinoline‐1‐acetonitrile in synthesis of 4H‐pyrido[2,1‐a]isoquinolines with antibacterial evaluation

“…Refluxing of Compound 1 with ethyl 3-aryl-2-cyanoacrylates 11a-f [30][31][32][33] in refluxing acetonitrile in the presence of piperidine to produce the corresponding 4H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile derivatives 12a-f (Scheme 3). The structures of isolated products were proven to be 12a-f on the basis of elemental analyses and spectral data.…”

Synthesis, and molecular modeling of bis(3-(piperazine-1-yl)propyl)tungstate (BPPT) nanoparticles, and its first catalytic application for one-pot synthesis of 4H-chromene derivatives

“…After characterization of the catalyst, with respect to the importance of using novel green and recyclable heterogeneous catalyst in chemical synthesis, herein, we decided to use and investigate the effectiveness of BPPT NPs in the synthesis of 4 H -chromene derivatives. In continues of our research studies on the synthesis and application of nanocatalysts in organic syntheses (Eskandari and Karami, 2018; Karami et al., 2013c; Pourshojaei et al., 2018b), we found that BPPT NPs can act as a potent, green and recyclable catalyst in an alternative two-step reactions that is Knoevenagel condensation and Michael reaction between methyl cyanoacetate ( 5 ), aryl aldehydes 6 and dimedone ( 7 ) to afford chromene derivatives 8 in good to excellent yields (Scheme 2).…”

“…Harmful effects of acidic work-ups can be removed by immobilization of aliphatic amines for example piperazine onto solid supports to obtain heterogeneous catalysts (Gupta et al., 2015). To profit from this technology, to date, various clean materials such as graphene (oxide) sheets (Eskandari and Karami, 2016; Khalili and Dehghani, 2016), silica or mesoporous silica (Pourshojaei et al., 2018b; Uruş et al., 2018), Fe 3 O 4 nanoparticles (Maleki et al., 2014), and dendrimer (Pullur Anil Kumar, 2010), have been using as support for preparation of new heterogeneous base catalysts to overcome the problems related to the homogeneous base catalysts.…”