Construction of Linked Nitrogen Heterocycles by Palladium(0)-Catalyzed Intramolecular Domino Cyclization of 2-Alkynylaziridines Bearing a 2-Aminoethyl Group via Ring Expansion with Isocyanate

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• 作者：Akinori Okano ; Shinya Oishi ; Tetsuaki Tanaka ; Nobutaka Fujii ; Hiroaki Ohno
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：May 21, 2010
• 年：2010
• 卷：75
• 期：10
• 页码：3396-3400
• 全文大小：777K
• 年卷期：v.75,no.10(May 21, 2010)
• ISSN：1520-6904

文摘

A novel palladium(0)-catalyzed domino cyclization of 2-alkynylaziridines with isocyanates through ring expansion is described. Treatment of N-protected 2-(4-aminobut-1-ynyl)aziridine derivatives with a catalytic amount of Pd(PPh₃)₄ and aryl isocyanates in THF at room temperature affords 4-(4,5-dihydropyrrol-2-yl)imidazolidin-2-one derivatives in good yields. Interestingly, bis-adducts were selectively obtained by use of excess isocyanate (5 equiv) at lower reaction temperature.