Synthesis of Fused Diaziridine Derivatives from Cyclic Secondary Amines by Utilizing N-Bromosulfonamides as an Aminating Reagent

被引：3

作者：

Kiyosu, Yuuki ^{[1
]}

Tanaka, Shino ^{[1
]}

Okumura, Sota ^{[1
]}

Kiyokawa, Kensuke ^{[1
]}

Minakata, Satoshi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Yamadaoka 2-1, Suita, Osaka 5650871, Japan

来源：

SYNTHESIS-STUTTGART | 2021年 / 53卷 / 17期

基金：

日本学术振兴会;

关键词：

cyclic secondary amines; cyclization; diaziridines; N-bromosulfonamides; nitrogen-containing heterocyclic compounds;

D O I：

10.1055/a-1468-8275

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of fused diaziridines, which are difficult to access by existing methods, was achieved by the reaction of cyclic secondary amines with p-toluenesulfonamide in the presence of N-bromosuccinimide (NBS) and a suitable base. This oxidation system enables the efficient in situ formation of the key intermediates, which are N-bromoamines (a precursor of cyclic imines) and N-bromosulfonamides. In addition, an alternative method using N-bromo-N-sodio-ptoluenesulfonamide (bromamine-T) in the presence of a catalytic amount of CF3CO2H for the synthesis of fused diaziridines is also reported.

引用

页码：3101 / 3109

页数：9

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