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Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines.

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.

SUBMITTER: Shea MT

PROVIDER: S-EPMC8659036 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines.

Shea Michael T MT Rohde Gregory T GT Vlasenko Yulia A YA Postnikov Pavel S PS Yusubov Mekhman S MS Zhdankin Viktor V VV Saito Akio A Yoshimura Akira A

Molecules (Basel, Switzerland) 20211203 23

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 <i>m</i>-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<sub>3</sub> and pyridine, these benziodazo ...[more]

PMID: 34885939

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