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

被引：4

作者：

Shea, Michael T. ^{[1
]}

Rohde, Gregory T. ^{[2
]}

Vlasenko, Yulia A. ^{[3
]}

Postnikov, Pavel S. ^{[3
]}

Yusubov, Mekhman S. ^{[3
]}

Zhdankin, Viktor V. ^{[1
]}

Saito, Akio ^{[4
]}

Yoshimura, Akira ^{[1
,3
]}

机构：

[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA

[2] Marshall Sch, Duluth, MN 55811 USA

[3] Tomsk Polytech Univ, Res Sch Chem & Appl Biomediacl Sci, Tomsk 634050, Russia

[4] Tokyo Univ Agr & Technol, Inst Engn, Div Appl Chem, Tokyo 1848588, Japan

来源：

MOLECULES | 2021年 / 26卷 / 23期

基金：

美国国家科学基金会; 俄罗斯科学基金会;

关键词：

hypervalent iodine; iodine heterocycles; benziodazolone; aroylation; ACID-CATALYZED REARRANGEMENT; HYPERVALENT IODINE REAGENTS; PEPTIDE-SYNTHESIS; TANDEM; CHEMISTRY; ACYLATION; ALDEHYDES;

D O I：

10.3390/molecules26237355

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：17

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