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  • Title: 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.
    Author: Okano A, Oishi S, Tanaka T, Fujii N, Ohno H.
    Journal: J Org Chem; 2010 May 21; 75(10):3396-400. PubMed ID: 20405897.
    Abstract:
    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(PPh(3))(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.
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