Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA.
Marshall School, Duluth, MN 55811, USA.
Molecules. 2021 Dec 3;26(23):7355. doi: 10.3390/molecules26237355.
Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with -chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed by X-ray analysis. In combination with PPh and pyridine, these benziodazolones can smoothly react with alcohols or amines to produce the corresponding esters or amides of 3-chlorobenzoic acid, respectively. It was found that the novel benziodazolone reagent reacts more efficiently than the analogous benziodoxolone reagent in this esterification.
高价碘杂环化合物是高价碘试剂的重要类别之一，在有机合成中有广泛的应用。本文报道了一种简便的合成苯并碘唑酮的方法，该方法是在室温下，用易得的碘代苯甲酰胺与 -氯过苯甲酸在乙腈中反应得到的。其中一个新的碘杂环化合物的结构通过 X 射线分析得到了确认。在三苯基膦和吡啶的存在下，这些苯并碘唑酮可以与醇或胺顺利反应，分别生成相应的 3-氯苯甲酸酯或酰胺。结果发现，在酯化反应中，新型苯并碘唑酮试剂比类似的苯并碘氮杂环酮试剂的反应活性更高。
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