One-pot synthesis of new alkyl 1-naphthoates bearing quinoline, pyranone and cyclohexenone moieties via metal-free sequential addition/oxidation reactions.

A mild and one-pot synthetic pathway was successfully developed for the synthesis of new naphthoate-based scaffolds containing quinoline, pyranone and cyclohexenone moieties via a multistep reaction between acenaphthoquinone and various 1,3-diketones in the presence of different primary aliphatic and benzylic alcohols. This reaction proceeds via a sequential addition/oxidation mechanistic process including a metal-free addition step of acenaphthoquinone and 1,3-diketones followed by the H5IO6-mediated C-C oxidative cleavage of the corresponding vicinal diols at room temperature. The alcohols play a dual role, as the reaction solvent as well as the nucleophile, to conduct the reaction process toward naphthoate formation. All alkyl naphthoate derivatives prepared in this work are new compounds and were definitively characterized using 1H-NMR, 13C-NMR and HRMS analysis, while X-ray crystallography was carried out for one of the products. The synthesis of a naphthalene-based nucleus attached to heterocyclic moieties is noteworthy to follow in the near future for diverse applications in biology, medicine, metal complex design, and semiconductor and optical materials.

One-Pot Synthesis of Spiro-isobenzofuran Compounds via the Sequential Condensation/Oxidation Reaction of Ninhydrin with 4-Amino-1,2-naphthoquinones/2-Amino-1,4-naphthoquinones under Mild Conditions.

A one-pot route for the synthesis of spiro-isobenzofuran compounds was developed via the condensation reaction of ninhydrin with 4-amino-1,2-naphthoquinones or 2-amino-1,4-naphthoquinones in acetic acid followed by the oxidative cleavage of the corresponding vicinal diols at room temperature. Various derivatives of spiro[benzo[g]indole-2,1'-isobenzofuran]-3,3',4,5(1H) tetraones and spiro[benzo[f]pyrrolo[2,3-h]quinoxaline-2,1'-isobenzofuran]-3,3'(1H)-diones were synthesized in good to high yields. Moreover, further condensation of spiro[benzo[g]indole-2,1'-isobenzofuran]-3,3',4,5(1H)-tetraones with 1,2-diamines resulted in the new spiro-isobenzofuran compounds having phenazine rings in high yields.

Metal-free syntheses of new azocines via addition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols.

A one-pot, clean and green procedure is described for the syntheses of new azocine derivatives via addition reactions of enaminones with acenaphthoquinone followed by periodic acid-mediated oxidative cleavages of the corresponding vicinal diols. Various derivatives of azocine were prepared and well characterized. The excellent yields, simple synthesis procedure, lack of a need to carry out any tedious work-up and column chromatography, metal-free catalysis, and mild reaction conditions are important features of this protocol.

Roughness-dependent wetting behavior of vapor-deposited metallic thin films.

We studied the wetting behavior of silver and copper thin films versus their kinetic roughening upon deposition at room temperature on glass substrates. Time-dependent height-height correlation functions were extracted from atomic force microscopy images, and they demonstrated a nonstationary growth front of the film roughness associated with a temporal evolution of the local surface slope. As a result, we tried to correlate the roughness statistical properties such as the root-mean-square (rms) roughness σ, the correlation length ξ, and the local surface slope (ρ≈σ/ξ) with the wetting behavior of the films' surfaces. The contact angle behavior was also studied by analyzing the variation of the energy of the system with water penetrating into the surface cavities, and the associated Laplace pressure induced by the local surface curvature. Hence, it was demonstrated that the wetting transition from a metastable Cassie-Baxter state to a Wenzel state as well as the penetration of a droplet into the surface crevices occur at the smaller local surface slopes for the higher surface energy material.

Chemometrics-assisted spectrophotometric method for simultaneous determination of Pb²âº and Cu²âº ions in different foodstuffs, soil and water samples using 2-benzylspiro [isoindoline-1,5'-oxazolidine]-2',3,4'-trione using continuous wavelet transformation and partial least squares - calculation of pKf of complexes with rank annihilation factor analysis.

A new multi-component analysis method based on zero-crossing point-continuous wavelet transformation (CWT) was developed for simultaneous spectrophotometric determination of Cu(2+) and Pb(2+) ions based on the complex formation with 2-benzyl espiro[isoindoline-1,5 oxasolidine]-2,3,4 trione (BSIIOT). The absorption spectra were evaluated with respect to synthetic ligand concentration, time of complexation and pH. Therefore according the absorbance values, 0.015 mmol L(-1) BSIIOT, 10 min after mixing and pH 8.0 were used as optimum values. The complex formation between BSIIOT ligand and the cations Cu(2+) and Pb(2+) by application of rank annihilation factor analysis (RAFA) were investigated. Daubechies-4 (db4), discrete Meyer (dmey), Morlet (morl) and Symlet-8 (sym8) continuous wavelet transforms for signal treatments were found to be suitable among the wavelet families. The applicability of new synthetic ligand and selected mother wavelets were used for the simultaneous determination of strongly overlapped spectra of species without using any pre-chemical treatment. Therefore, CWT signals together with zero crossing technique were directly applied to the overlapping absorption spectra of Cu(2+) and Pb(2+). The calibration graphs for estimation of Pb(2+) and Cu (2+)were obtained by measuring the CWT amplitudes at zero crossing points for Cu(2+) and Pb(2+) at the wavelet domain, respectively. The proposed method was validated by simultaneous determination of Cu(2+) and Pb(2+) ions in red beans, walnut, rice, tea and soil samples. The obtained results of samples with proposed method have been compared with those predicted by partial least squares (PLS) and flame atomic absorption spectrophotometry (FAAS).

Simultaneous spectrophotometric determination of Cd2+, Cu2+, and Zn2+ in rice and vegetal samples with dimethyl-spiro[isobenzofurane-1,6'-pyrorolo[2,3-d]pyrimidine]-2',3,4,5'(1'H,3'H,7'H)tetraone using wavelet transformation-feed forward neural networks.

A multicomponent analysis method for the simultaneous spectrophotometric determination of the Cd(2+), Cu(2+), and Zn(2+) based on complex formation with dimethyl-spiro[isobenzofurane-1,6'-pyrorolo[2,3-d]pyrimidine]-2',3,4,5'(1'H,3'H,7'H)tetraone using wavelet transformation-feed forward neural network is proposed. The analytical data showed that metal to ligand ratios in all metal complexes was 1:1. The absorption spectra were evaluated with respect to synthetic ligand concentration and pH. It was found that, at pH 6.7, the complexation reactions were completed. Spectral data were reduced using continuous wavelet transformation (CWT) and subjected to artificial neural networks. The presence of nonlinearities was confirmed by a partial response plot. The structures of the CWT-feed forward neural networks (WT-FFNN) were simplified using the corresponding wavelet coefficients of mother wavelets. Once the optimal wavelet coefficients are selected, different ANN models can be employed for the calculation of the final calibration model. The proposed methods were successfully applied to the simultaneous determination of Cd(2+), Cu(2+), and Zn(2+) in rice, dill, tomato, and lettuce samples.