Formal Ring Contraction of Cyclic N-Sulfonamides via C-N Bond Cleavage and α-Amination by Oxidation of Halides

被引：9

作者：

Nishiguchi, Yuna ^{[1
]}

Tomizuka, Akihiko ^{[1
]}

Moriyama, Katsuhiko ^{[1
]}

机构：

[1] Chiba Univ, Dept Chem, Grad Sch Sci & Soft Mol Activat, Res Ctr,Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 23期

关键词：

alpha-Amination; C-N Bond Cleavage; Halogen; Oxidation; Ring Contraction; ALKALI-METAL BROMIDE; CARBONYL-COMPOUNDS; CATALYSIS; AMINES; CYCLIZATION; INHIBITORS; UMPOLUNG;

D O I：

10.1002/adsc.202001034

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An oxidative C-N bond cleavage reaction of substituted cyclic sulfonamides that proceeds via oxidation of bromide ion in hydrogen bromide solution was developed to furnishN-sulfonamide-protected acyclic amino ketones in high yields. The subsequent alpha-amination of the amino ketones via the oxidation of iodide in tetrabutylammonium iodide provided 2-acyl cyclic sulfonamides in good yields. The combination of these transformations involving the oxidation of halides resulted in a formal ring contraction of substituted cyclic amides.

引用

页码：5518 / 5523

页数：6

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