|
|||||
|
|
Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines |
|
| Authors: | Michael T Shea Gregory T Rohde Yulia A Vlasenko Pavel S Postnikov Mekhman S Yusubov Viktor V Zhdankin Akio Saito Akira Yoshimura |
| Institution: | 1.Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA;2.Marshall School, Duluth, MN 55811, USA;3.Research School of Chemisty and Applied Biomediacl Sciences, The Tomsk Polytechnic University, 634050 Tomsk, Russia; (Y.A.V.); (P.S.P.); (M.S.Y.);4.Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan |
| Abstract: | 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 m-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 PPh3 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. |
| Keywords: | hypervalent iodine iodine heterocycles benziodazolone aroylation |