Porous chitosan–MnO2 nanohybrid: a green and biodegradable heterogeneous catalyst for aerobic oxidation of alkylarenes and alcohols

A porous chitosan–manganese dioxide (PC–MnO₂) nanohybrid was synthesized using an in situ reduction method, in which potassium permanganate solution and nanoporous chitosan acted as precursor and reducing agent. The chemical and structural properties of PC–MnO₂ were characterized using scanning and transmission electron microscopies, X‐ray diffraction, thermogravimetric analysis and Fourier transform infrared spectroscopy. Highly dispersed MnO₂ nanoparticles in a matrix of porous chitosan showed high catalytic activity for selective aerobic oxidation of alkylarenes and alcohols without using any bases or expensive oxidants. Short reaction time, ease of product separation by filtration and recyclability of the catalyst make it environmentally and economically favoured for the synthesis of versatile aldehydes and ketones. Copyright © 2015 John Wiley & Sons, Ltd.     

Anion‐binding properties of two calix[4]arene derivatives containing two ferrocene imine or ferrocene amine units at the upper rim

Calix[4]arene derivatives containing ferrocene units at the upper rim have been synthesized and their anion‐binding and sensing investigated towards anions such as chloride, bromide and hydrogen sulfate by cyclic voltammetry. Electrochemical studies show that these redox‐active ligands electrochemically recognize chloride and bromide anions. These compounds have excellent selectivity for chloride and bromide ions, in the comparison with hydrogen sulfate anion. With ferrocenyl Schiff base calix[4]arene 1 an anodic shift as large as 302 mV is observed on addition of four equivalents of Cl⁻ anion. Also electrochemical and UV–vis spectroscopic titrations ferrocenyl calix[4]arene derivatives 1 with chloride and bromide ions and 2 (only with Cl⁻) indicate a 1:1 binding‐stiochiometry. Copyright © 2011 John Wiley & Sons, Ltd.     

A green synthesis of nitrones from diamino glyoxime using aldehydes and ketones

The reaction of diaminoglyoxime with aldehyde and ketone derivatives in the presence of p-toluene sulphonic acid in H₂O–MeOH mixture at room temperature afforded nitrone derivatives in high yields within 10–140 min. The applicability of ketones in this reaction for the preparation of novel nitrones has been verified. The effect of the temperature on the stability of the structural isomers of the products has been studied by NMR as well. The results showed that, at high temperatures only one product could be observed. The nature of solvent and catalyst were evaluated and found that the strong acids H₂SO₄ and CF₃SO₃H in protic solvent CH₃OH work well while neither CH₃SO₃H in protic solvent nor p-toluene sulphonic acid in aprotic solvents toluene and THF perform the same reactions.     

The solvent‐free synthesis of polysubstituted pyrroles by a reusable copper Schiff base complex immobilized on silica coated Fe3O4, and DNA binding study of one resulting derivative as a potential anticancer drug

We demonstrate herein the synthesis of a new copper Schiff base complex immobilized on silica‐coated Fe₃O₄ nanoparticles. The structure and composition of this magnetic nanocatalyst were analyzed using Fourier transform infrared (FT‐IR), X‐ray powder diffraction (XRD), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM), energy dispersive X‐ray (EDX) and inductively coupled plasma atomic emission spectroscopy (ICP‐AES). This nanocomposite was found to be an efficient nanocatalyst for the synthesis of polysubstituted pyrrole derivatives and the products were isolated with high turnover number (TON) and high to excellent yields. Among the new synthesized polysubstituted pyrrole derivatives, we explored the first computational and experimental binding study of methyl 1‐benzyl‐4‐(furan‐2‐yl)‐2‐methyl‐1H‐pyrrole‐3‐carboxylate (SP‐10) with calf thymus deoxyribonucleic acid (ct‐DNA), suggesting their application as potential anticancer activity. In addition, the binding modes of SP‐10 with DNA and human serum albumin (HSA) were verified by molecular docking technique.     

A novel one-pot pseudo five-component isocyanide-based reaction: synthesis of 2,6-bis(alkylamino)-benzofuro[5,6-b]furan-4,8-dione derivatives

A novel one-pot pseudo five-component reaction of isocyanides with 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione and various aliphatic and aromatic aldehydes in ethanol at room temperature has been studied. 2,6-Bis(alkylamino)-benzofuro[5,6-b]furan-4,8-dione derivatives were isolated as the products in good yields after 24 h.     

Synthesis of a New Library of Pyrano‐phenazine Derivatives via a Novel Three‐Component Protocol

The pyrano‐phenazine derivatives 6 were synthesized by an efficient procedure using the reaction between benzo[a]phenacin‐5‐ols with the condensation product of an aldehyde with Meldrum's acid in the presence of a catalytic amount of Et₃N at ambient temperature. The procedure is very simple, and products could be separated from the reaction media by simple filtration. High functional‐group tolerance both in the benzo[a]phenazin‐5‐ol and aldehyde moieties, facile reaction procedure, medium‐to‐high yields, and simple separation of the products from the reaction media are the advantages of this route.     

Isocyanide‐Catalyzed Reaction of Tetracyanoethylene and Activated 1,3‐Dicarbonyl CH‐Acid Compounds: A Rapid and Efficient Synthesis of Pyran Annulated Heterocyclic Systems

An isocyanide‐catalyzed reaction between tetracyanoethylene and various activated CH‐acid compounds to afford the corresponding pyran annulated heterocyclic ring systems, in high yield at room temperature within a few minutes, is described. To the best of our knowledge, this is the first example in which isocyanide functions as only a catalyst but not a reagent.     

1,1,3,3‐N,N,N′,N′‐Tetramethylguanidinium Trifluoroacetate Ionic Liquid–Promoted Efficient One‐Pot Synthesis of Trisubstituted Imidazoles

Trisubstituted imidazoles have been synthesized in very short reaction times with excellent yields in the presence of 1,1,3,3‐N,N,N′,N′‐tetramethylguanidinium trifluoroacetate as an ionic liquid at 100°C. The ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency.     

Electro-Organic Synthesis of 2-Amino-3-cyano-benzofuran Derivatives Using Hydroquinones and Malononitrile

Abstract

In this work, electrochemical oxidation of hydroquinones has been studied in the presence of malononitrile as a nucleophile in aqueous solution using cyclic voltammetry and controlled potential coulometry. The results indicate that the quinones derived from hydroquinones participate in Michael addition and then intramolecular nucleophilic addition to yield benzofuran derivatives. The electrochemical synthesis of these new 2-amino-3-cyano-benzofuran derivatives has been performed successfully at a carbon-rod electrode in an undivided cell in good to excellent yields at room temperature.