Rapid Synthesis of 3‐Aminoimidazo[1,2‐a]Pyridines and Pyrazines

p‐Toluenesulfonic acid catalyzed the one‐pot, three‐component synthesis of 3‐aminoimidazo[1,2‐a]pyridines and pyrazines through a condensation reaction of a 2‐aminoazine, an aldehyde, and an isocyanide at room temperature. This methodology affords a number of 3‐aminoimidazo[1,2‐a]pyridines in reasonable yields and short reaction times without any significant optimization of the reaction conditions.     

An Easy One-Pot Procedure for the Synthesis of N -Sulfonyl Phosphorous Ylides and Sulfonyl Iminophosphoranes

Reaction of triphenylphosphine and an electron deficient acetylenic ester in the presence of strong N–H acid such as alkyl and aryl sulfamides or acetamide produces phosphorous ylides at room temperature in CH₂Cl₂. The aryl sulfamide phosphoranes undergo a smooth transformation reaction in boiling toluene and produce iminophosphoranes.     

Synthetic–Natural Bionanocomposite Hydrogels on the Basis of Polyvinyl Alcohol and Egg White

A series of bionanocomposite hydrogels composed of polyvinyl alcohol, a synthetic polymer, and egg white, a natural protein containing material, were prepared by the freezing- thawing cyclic method. Na-montmorillonite nanoclay (Na-MMT), as a crosslinker and reinforcing agent, with 0, 5, 10, and 15 wt% loadings (based on the dried mass of the bionanocomposite hydrogel) was incorporated in the polyvinyl alcohol and egg white hydrogel matrix. The microstructural characteristics of the prepared bionanocomposite hydrogels were characterized by the X-ray diffractometry, transmission electron microscopy, Fourier transform infrared spectroscopy, scanning electron microscopy and gel fraction measurements. Thermal and mechanical properties of the samples were also studied using differential scanning calorimetry and dynamic mechanical-thermal analysis. The swelling and drying kinetics and mechanisms of the bionanocomposite hydrogels were also studied. The bionanocomposite hydrogels had an exfoliated Na-MMT morphology with an appropriate dispersion of nanoclay layers in the hydrogel matrix. The results showed that the Na-MMT platelets acted as crosslinkers and created a hydrogel network with a smaller pore size in the bio-nanocomposite hydrogels, compared with the clay-free hydrogel. The obtained thermal and mechanical properties confirmed the reinforcing effect of the nanoclay in the bionanocomposite hydrogels. The swelling and drying rates of the bionanocomposite hydrogels exhibited an inverse dependency on the nanoclay loading. In general, it was concluded that the prepared bionanocomposite hydrogels could be used as appropriate biomaterials in biomedical applications, especially in drug delivery, tissue engineering and wound care.     

Ionic liquid promoted selective oxidation of organic compounds with NaBrO3

1-Butyl-3-methylimidazolium bromide ([bmim]Br) as an ionic liquid promoted selectively the oxidation of alkyl arenes and alcohols to the corresponding carbonyl compounds with NaBrO₃ in excellent yields under neutral conditions at the 70°C. Among the various ionic liquids examined, the [bmim]Br exhibited the best performances with NaBrO₃. The ionic liquid can be recycled and reused for several runs without any significant loss of activity. Correspondence: Ahmad Shaabani, Department of Chemistry, Shahid Beheshti University, P.O. Box 19839-4716, Tehran, Iran.     

Silica-supported cobalt(II) tetrasulfophthalocyanine catalyzed aerobic oxidation of thiols to disulfides under neutral conditions

A very simple and mild reaction is described for the aerobic oxidative coupling of thiols to disulfides by silica-supported cobalt(II) tetrasulfophthalocyanine as the catalyst in non-aqueous media under neutral conditions at room temperature. The catalyst can be reused for the oxidative coupling of several thiols without any significant loss of catalytic activity. Correspondence: Ahmad Shaabani, Department of Chemistry, Shahid Beheshti University, P.O. Box 19396, 4716 Tehran, Iran.     

Frontier orbitals aromaticity: A simple approach to the analysis of pericyclic reactions

A new and simple approach to the analysis of pericyclic reactions based on combination of the interaction of HOMO-LUMO molecular orbitals and Huckel-Mobius aromaticity concept in transition state is reported. This approach seems to be more powerful than the Woodward-Hoffmann approach which appears to be limited to reactions with sufficiently high symmetry, and the Huckel-Mobius that use the non-participating lowest basis set (Ψ₁). One important impact of the current approach is its capability in addressing the photochemical concerted reactions.     

Synthesis of 1-aminoimidazo[5,1-a]isoquinolinium salts based on multicomponent reactions of isocyanides

A novel pseudo-four-component condensation yielding 1-aminoimidazo[5,1- a]isoquinolinium salts from isocyanides, isoquinoline, and sulfonic or bromic acids is described. The method offers several advantages including high yields of products and an easy experimental workup procedure.     

Synthesis of a novel class of 3‐(2′‐benzothiazolyl)‐2,3‐dihydroquinazolin‐4(1H)‐ones under solvent‐free and catalyst‐free conditions

A solvent‐ and catalyst‐free one‐pot three‐component condensation reaction approach was developed for the synthesis of a new class of 3‐(2′‐benzothiazolyl)‐2,3‐dihydroquinazolin‐4(1H)‐ones in relatively good yields.     

A novel isocyanide-based three-component reaction: synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives

A novel multi-component synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives starting from simple and readily available inputs is described. Thus, simply stirring an ethanol solution of 2,3-diaminomaleonitrile, a ketone, and an isocyanide in the presence of a catalytic amount of p-toluenesulfonic acid provided highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives in good to excellent yields at ambient temperature.     

Synthesis,characterization and extraction properties of calix[4]crown with amine units and study of its complexes with Cu(II)

In this work, we have focused on the synthesis of p-tert-butyl calix[4]crown with amine units (H ₃ L) as a class of selective receptors for metal ions. The macrocyclic ligand (H ₃ L) with N₂O₇ donors was synthesized via condensation between 1,3-diaminocalix[4]arene and 2-[3-(2-formylphenoxy)-2-hydroxypropoxy] benzaldehyde, followed by reduction of the Schiff base product in situ with sodium borohydride, then it was characterized by FT-IR, ¹H NMR and X-ray crystallography. Two Cu(II) complexes were prepared from the reaction of H ₃ L with Cu(II) salts (CuX₂, X = ClO₄ ^? and Cl^?). FT-IR, UV–Vis, elemental analysis, molar conductivity and cyclic voltammetry techniques were used for study and characterization of these complexes. On the basis of liquid–liquid extraction experiments, ligand H ₃ L indicated good affinity toward Pb²⁺ and Cu²⁺.