Selective Synthesis of Eight-Membered Cyclic Ureas by the [6+2] Cycloaddition Reaction of 2-Vinylazetidines and Electron-Deficient Isocyanates

被引：29

作者：

Koya, Shunsuke ^{[1
]}

Yamanoi, Kenichi ^{[1
]}

Yamasaki, Ryu ^{[1
]}

Azumaya, Isao ^{[2
]}

Masu, Hyuma ^{[2
]}

Saito, Shinichi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Tokushima Bunri Univ, Fac Pharmaceut Sci Kagawa Campus, Kagawa 7692193, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 23期

关键词：

RING-EXPANSION; REARRANGEMENT; AZIRIDINES; CYCLIZATION; ROUTE;

D O I：

10.1021/ol902299p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [6 + 2] cycloaddition reaction of 2-vinylazetidines with electron-deficient isocyanates such as tosyl Isocyanate proceeded smoothly in the absence of the catalyst at room temperature, and various cyclic ureas were isolated in good to high yields. Electron-deficient allenes also reacted with the 2-vinylazetidine, and the corresponding azocine derivatives were isolated.

引用

页码：5438 / 5441

页数：4

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