[5 + 2] Cycloaddition Reaction of 2-Vinylaziridines and Sulfonyl Isocyanates. Synthesis of Seven-Membered Cyclic Ureas

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• 作者：Eri Kanno ; Kenichi Yamanoi ; Shunsuke Koya ; Isao Azumaya ; Hyuma Masu ; Ryu Yamasaki ; Shinichi Saito
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：March 2, 2012
• 年：2012
• 卷：77
• 期：5
• 页码：2142-2148
• 全文大小：310K
• 年卷期：v.77,no.5(March 2, 2012)
• ISSN：1520-6904

文摘

The [5 + 2] cycloaddition reaction of 2-vinylaziridines with sulfonyl isocyanates proceeded smoothly under mild conditions, and various cyclic ureas were isolated in high yields. The remarkable solvent effect on the reaction was observed, and the preferential formation of the seven-membered ring occurred when the reaction was carried out in CH₂Cl₂. The scope and limitation were studied, and the mechanism of this reaction was discussed. This study provides a new and simple method for the synthesis of seven-membered cyclic ureas.