Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate

Aryl sulfones have been synthesized by the reaction of sodium p-toluenesulfinate and arenediazonium salts using a CuI catalyzed homogeneous system.

Facile Synthesis and Antimicrobial Evaluation of Some New Heterocyclic Compounds Incorporating a Biologically Active Sulfamoyl Moiety

A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reactedin situwith chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, keteneN,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.

Synthesis, properties and color assessment of some new 5-(3- and 4-substituted phenylazo)-4,6-dimethyl-3-cyano-2-pyridones

A series of 5-(3- and 4-substituted phenylazo)-4,6-dimethyl-3-cyano-2-pyridones were synthesized, starting from acetylacetone and arenediazonium salt, followed by condensation with cyanoacetamide using a modified literature procedure. The experimental investigation included modification of the synthetic procedure in terms of solvent, temperature, isolation techniques as well as purification and identification of the products. The azo dyes were characterized by melting point, IR, UV/Vis, 1H NMR and MS data. HPLC analyses were also performed. The 2-hydroxypyridine/ 2-pyridone tautomeric equilibration was found to depend on the polarity of the applied solvents. A color assessment of the solid dyes and dyed polyester fabrics was also performed and the correlation between the colour and the structure of the dyes is discussed.