Abstract
AbstractA metal‐free cascade annulation of propagylamines with amidines for divergent synthesis of polysubstituted imidazoles and 4‐alkenylquinazolines has been developed. The reaction is believed to proceed by sequential 1,4‐conjugate addition of amidines to propargylamines, 5‐exo‐dig annulation/aromatization to form the polysubstituted imidazoles, and nucleophilic addition/elimination/aromatization to quinazoline skeleton. In this reaction, a broad range of electron‐rich, electron‐neutral, and electron‐deficient propagylamines react well with amidines to give polysubstituted imidazoles and 4‐alkenylquinazolines in 53–93% yields. Moreover, the utility of this method was showcased by gram‐scale experiments and synthetic transformations of the product.magnified image
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