A range of acyl azoles have been prepared from aromatic, heteroaromatic, and aliphatic aldehydes by means of an oxidative amidation reaction. The methodology employs a substoichiometric quantity of an oxoammonium...
Novel acyl pyrazoles and acyl triazoles have been prepared by means of the oxidative amidation of aldehydes in the presence of the requisite azole. Yields range from modest to good in both cases, and some limitations of the substrate scope have been discovered. Acyl pyrazoles were prepared by treatment of a mixture of aldehyde and pyrazole with an oxoammonium salt bearing the nitrate anion. In the case of acyl triazoles, the oxidative functionalization was performed using sodium persulfate as a terminal oxidant in the presence of a catalytic quantity of a nitroxide.
The acyl pyrazole derivative (3,5-di-tert-butylphenyl)(1H-pyrazol-1-yl)methanone was prepared simply and rapidly in 86% isolated yield by means of an oxidative functionalization reaction of an aldehyde with pyrazole. A substoichiometric quantity of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium nitrate was used as the oxidant. The reaction was performed solvent-free and in the absence of a base, making it a clean, green approach. The mixture of aldehyde, pyrazole, and the oxidant was heated at 55 掳C for 3 h, and then, the product was isolated in analytically pure form via extraction with no need for column chromatography.
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