Synthesis of ene-1,1-diamines and pyrrolo [1,2-a] imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening

Jones, Raymond C.F., Martin, Jason N., Smith, Paul, Gelbrich, Tomas, Light, Mark E. and Hursthouse, Michael B. (2000) Synthesis of ene-1,1-diamines and pyrrolo [1,2-a] imidazolediones by 4,5-dihydroimidazole N-oxide cycloaddition and isoxazoline ring opening. Chemical Communications, (19), 1949-1950. (doi:10.1039/b005530l).

Abstract

Dihydroimidazole N-oxides 1 undergo 1,3-dipolar cycloaddition with alkyne dipolarophiles and the cycloadducts suffer isoxazoline N-O bond cleavage to afford ene-1,1-diamines, with subsequent cyclisation to pyrrolo[1,2-a]imidazole-5,6-diones if possible.

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