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Relevant academic research and scientific papers

Magnetic Fe3O4 nanoparticles as efficient and reusable catalyst for the green synthesis of 2-Amino-4H-chromene in aqueous media

A simple and efficient protocol for one-pot three-component coupling of aldehyde, malononitrile, and resorcinol in water using magnetically recoverable Fe3O4 nanoparticles at room temperature is reported. The high yields of products and short reaction time were attributed to the nanosize of about 18nm in which the catalyst could act as a nanoreactor. This methodology is found to be fairly general and catalyst is easily separated by magnetic devices and can be reused without any apparent loss of activity for the reaction.

Biocompatible Ionic Liquid Promote One-Pot Synthesis of 2-Amino-4H-Chromenes Under Ambient Conditions

Abstract: The synthesis of 2-amino-4H-chromenes through one-pot multicomponent reactions has received great attention due to the high atom efficiency and the broad bioactivities of the products. Here, the catalytic performances of a series of functional ionic liquids towards this type of reaction were investigated and the results showed that the ionic liquid, choline acetate ([Choline][Ac]), could efficiently promote this reactions under room temperature without the necessary of organic solvents. The reaction is easy to be conducted and the following work-up procedures are very simple. The pure products can be obtained through extraction and washing procedures, no column separation procedures are needed. Intriguingly, this reaction system can be easily scaled up to multi-gram, suggesting its perspective in industrial applications. In addition, the ionic liquid [Choline][Ac] can be easily prepared from cheap and biocompatible materials, and it can be feasibly recycled and reutilized for at least five cycles. Graphic Abstract: Various aldehydes, malononitrile and activated phenols could be converted to thecorresponding 2-amino-4H-chromenes with good to excellent isolated yields underthe catalysis of choline acetate at room temperature. [Figure not available: see fulltext.]

Green protocol for synthesis of MgFe2O4 nanoparticles and study of their activity as an efficient catalyst for the synthesis of chromene and pyran derivatives under ultrasound irradiation

In this study, the MgFe2O4 nanoparticles were synthesized via a green and simple approach. Then an effective procedure to synthesize 2-amino-7-hydroxy-4H-chromene and tetrahydrobenzo[b]pyran derivatives was established through the ch

Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions

A series of new prolinamide polyacrylonitrile fiber catalysts with tunable length of alkyl linker and different linker group were prepared by covalent bonding for the first time and well characterized by mechanical strength, FT-IR, XRD, EA, TGA, SEM and water contact angel. The catalytic activities of these fiber catalysts were evaluated in Knoevenagel condensation and one-pot Knoevenagel-Michael multicomponent tandem reactions to synthesize α, β-unsaturated nitrile and 2-amino-4H-chromene derivatives in water. The result show that the suitable linker length attaching amines to fiber matrix as well as the constructed hydrophobic microenvironment by linker group within the surface layers of fiber materials effectively promotes the reactions. In addition, the good swollen capacity of fiber in solvent ensure that the reaction proceed well. Fiber catalyst PANPA?2F modified by prolinamide with a C2 alkyl chain exhibited the best catalytic performance and can be easily recovered and reused for at least ten consecutive cycles without significant loss of catalytic activity and active sites leaching.

Novel ferrocene substituted benzimidazolium based ionic liquid immobilized on magnetite as an efficient nano-catalyst for the synthesis of pyran derivatives

Due to the attractive applications of functionalized ionic liquids (ILs) based on benzimidazolium as catalysts or solvents in the chemical reactions and also the wide applications of benzimidazole-based compounds in the medicinal chemistry; we designed an

Novel task-specific ionic liquid [Et2NH(CH2)2CO2H][AcO] as a robust catalyst for the efficient synthesis of some pyran-annulated scaffolds under solvent-free conditions

A novel task-specific ionic liquid, 2-carboxy-N,N-diethylethanaminium acetate denoted as [Et2NH(CH2)2CO2H][AcO], is prepared in an easy process and fully characterized by using suitable methods such as FT-IR, 1H-NMR, 13C-NMR, and TG, DTG and DTA analyses. After preparation, the promoting ability of this catalyst for one-pot multicomponent synthesis of 2-amino-4H-chromenes, dihydropyrano[3,2-c]chromenes and dihydropyrano[2,3-c]pyrazoles using in situ-developed arylidenemalononitriles through Knoevenagel reaction under solvent-free conditions is described. The sustainable procedure, short reaction times (6–36?min), effortless work-up, non-chromatographic purification, good-to-excellent product yields (79–96%), ease of recovery and reusability of the catalyst up to six reaction runs without a decrease of activity are the notable features of the present protocol.

Method for preparing 2-amino-4H-chromene derivative by one-pot method promoted by hydrogen bond functionalized ionic liquid

The invention discloses a method for preparing a 2-amino-4H-chromene derivative by one-pot method promoted by a hydrogen bond functionalized ionic liquid. According to the method, a phenol compound, an aromatic aldehyde compound and malononitrile are used

Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene?D-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities

The series of 2-amino-7-propargyloxy-4H-chromene-3-carbonitriles 5a-t were synthesized from corresponding 2-amino-7-phydroxy-4H-chromene-3-carbonitriles 4a-t and propargyl bromide. Two procedures were used in these syntheses: K2CO3/acetone and NaH/DMF procedures with yields of 65–89% and 80–96%, respectively. 1H-1,2,3-Triazole-tethered 4H-chromene?D-glucose conjugates 7a-t were synthesized using click chemistry of propargyl ethers 5a-t and tetra-O-acetyl-β-D-glucopyranosyl azide. Cu@MOF-5 was the optimal catalyst for this chemistry. The yields of 1H-1,2,3-triazoles were 80–97.8%. All triazoles 7a-t were evaluated in vitro for anti-microorganism activities. Among tested compounds with MIC values of 1.56–6.25 μM, there were four compounds against B. subtilis, four compounds against S. aureus, and four compounds against S. epidermidis; five compounds against E. coli, four compounds against K. pneumoniae, five compounds against P. aeruginosa, and six compounds against S. typhimurium. Compounds 7c,7d,7f,7h, and 7r had MIC values of 1.56–6.25 μM for three clinical MRSA isolates. Some compounds had inhibitory activities against four fungi, including A. niger, A. flavus, C. albicans, and S. cerevisiae, with MIC values of 1.56–6.25 μM. Some 1H-1,2,3-triazoles had comparatively low toxicity against RAW 264.7 cells.

Synthesis and structure of some substituted 2-amino-4-aryl-7-propargyloxy-4H-chromene-3-carbonitriles

A series of 2-amino-7-hydroxy-4H-chromene-3-carbonitriles 4a–l were synthesized through three-component reaction using sodium carbonate as a catalyst. The reaction was carried out in 96% ethanol-water medium (1:20 ratio in volume). Propargyl ether compounds 5a–l of these chromene-3-carbonitriles were successfully synthesized from corresponding hydroxyl chromene derivatives by reaction with propargyl bromide. Two different procedures were applied in this process: the procedure that used potassium carbonate in dried acetone and the procedure that used sodium hydride in dried DMF. The latter gave the ethers 5a–l in higher yields. The single-crystal X-ray structure of propargyl ether 5g has been recorded.

Aqua-mediated multicomponent synthesis of various 4H-pyran derivatives catalyzed by poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst

A green and efficient approach for synthesis of some new 4H-pyran derivatives is reported, catalyzed by green recyclable poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst in water. This procedure has many advantages such as operational s