A one-pot synthesis of 1,2,4,5-tetraarylimidazoles using molecular iodine as an efficient catalyst

Molecular iodine is a cheap, nontoxic catalyst, which acts as an efficient catalyst for the synthesis of 1,2,4,5-tetraarylimidazoles using benzoin, an aromatic aldehyde and an amine in the presence of ammonium acetate. The advantage of this method is the direct use of benzoin, which is transformed into benzil in situ and condenses further to generate the imidazole in a one-pot sequence.     

Solubility of benzil in binary alkane + dibutyl ether solvent mixtures. Comparison of predictive expressions derived from the nearly ideal binary solvent model

Experimental solubilities are reported for benzil dissolved in six binary mixtures containing dibutyl ether with hexane, heptane, octane, cyclohexane, methylcyclohexane, and 2,2,4-trimethylpentane at 25°C. Results of these measurements are compared to the predictions of equations developed previously for solubility in systems of nonspecific interactions. The most successful equation in terms of goodness of fit involved a volume fraction average of the excess Gibbs energies relative to the Flory-Huggins model, and predicted the experimental solubilities in the six systems studied to within an overall average absolute deviation of 3.4% and with a maximum deviation of 6.0%.     

Samarium reagent-promoted formation of benzoins from diarylmethanones and DMF via a carbene rearrangement reaction

Prompted by samarium metal in DMF with TMSCl or iodine as an activator, or by SmI₂/THF system, diarylmethanones react readily with DMF to afford benzoins in moderate to good yields via rearrangement of aryl groups. As for asymmetric diarylmethanones, products resulting from the migration of either aryl group were obtained, where the migration of aryl groups shows certain priority.     

Tandem and chemoselective synthesis of benzil derivatives from styrene and arene diazonium salts

A facile and practically applied protocol for synthesis of benzil derivatives using styrene and arene diazonium salts is reported. Pd(OAc)₂/SeO₂ catalytic system was found to be efficient for chemoselective synthesis of benzil. Selenium dioxide works well as an oxidant under milder reaction conditions. Moderate to very good yields of the desired products were obtained.     

One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Using MoO3/SiO2, an Efficient and Recyclable Catalyst

A simple one-pot synthesis has been developed for the synthesis of 2,4,5-trisubstituted imidazoles using an efficient and recyclable MoO₃/SiO₂ solid acid catalyst by condensation of benzil or benzoin, benzaldehyde, and ammonium acetate in acetonitrile as a solvent. Using this solid catalyst, the reactions could be carried out under mild reaction conditions with very good yield of imidazoles, up to 95%. This catalyst could be recycled very easily, which makes this methodology environmentally benign.     

Facile Synthesis of Bis(crown ether)benzils: Prospective Building Blocks for Metal Ion Sensors

A new facile synthetic route to benzils containing fragments of 12-crown-4, 15-crown-5, and 18-crown-6 by oxidation of corresponding stilbenes was developed. The first representative of a new family of fluorescent sensors was obtained by reaction of bis(15-crown-5)benzil with o-phenylenediamine. The latter exhibits great fluorescence enhancement upon association with K⁺ and Rb⁺ compared to Na⁺ and Cs⁺.     

Laser induced optoacoustic spectroscopy of benzil: Evaluation of structural volume change upon photoisomerization

The cis-skew to trans-planar photoisomerization of benzil in the photoexcited state was studied by laser-induced optoacoustic spectroscopy (LIOAS) in a series of normal alkane solvents at room temperature. The structural volume change due to the photoisomerization process has been estimated and compared with the same calculated from the optimized skew and trans structures. The magnitude of the structural volume change is estimated to be 22.9 ± 1.2 mL/mol. This study reveals that an expansion in volume occurs during the photoinduced isomerization process. In non-polar alkane solvents, the estimated volume change has been argued to be free from electrostrictional contribution.     

Catalyst-free and solvent-free method for the synthesis of quinoxalines under microwave irradiation

A facile procedure for the synthesis.of quinoxalines is being reported starting from benzil and 1,2-diaminobenzene. Thereactions were carried out catalyst-free, solvent-free and under microwave irradiation conditions in high yield (84-98%) with short time (3-6 rain) and environmental benign, as well as convenient operation. The structures of all the compounds have been confirmed on the basis of their IR, 1H NMR, and/or 13C NMR, mass spectral data.     

Sodium Bisulfite as an Efficient and Inexpensive Catalyst for the One-pot Synthesis of 2,4,5-Triaryl-1<Emphasis Type="Italic">H</Emphasis>-imidazoles from Benzil or Benzoin and Aromatic Aldehydes

Summary. 2,4,5-Triaryl-1H-imidazoles were efficiently synthesized from benzoin or benzil, ammonium acetate, and aromatic or heteroaromatic aldehydes in the presence of sodium bisulfite as catalyst. The present protocol offers significant improvements for the synthesis of 2,4,5-triaryl-1H-imidazoles with regard to yield of products, simplicity in operation, and cheap catalyst.     

Spectral Studies and Cathodic Reduction of some Thiazolylazo Derivatives

The structure of the 2-thiazolylazosalicylic acid molecule, TAS, has been determined by means of quantum SCF-CI calculations. The ionization potential and the electron affinity of TAS molecule were calculated to have the values 9.057 and 2.56 eV respectively. The solvation energies in different solvents, and the bond orders of the TAS molecule were calculated for the neutral state, the oxidized form (the cation) and the reduced form (the anion). Mixed solvent studies were carried out with TAS and 2-benzothiazolylazosalicylic acid (BTAS), using polar solvents (EtOH and MeOH) to confirm the formation of a solvent-solute complex. The azo group in the TAS molecule nas a considerable contribution in the SCFLUMO; thus cathodic reduction has been focused on the azo group and was verified experimentally by cathodic reduction.