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ChemInform Abstract

Synthesis of title vinylquinazolinones (IV) is smoothly achieved by base-catalyzed cyclization of the corresponding o-(ω-halopropionyl)aminobenzoic acid amides (III). Compounds (IVa) and (IVb) are good Michael acceptors that undergo reactions with various C- or N-nucleophiles at the vinyl group to furnish the corresponding adducts, e.g. (VI), (VIII), and (X). Halo-substituted vinylquinazolinones (IVc) and (IVd) are also good Michael acceptors, but due to secondary reactions like dehydrohalogenation or cyclization other products are obtained, e.g. cyclopropane (XII) or furan derivatives like (XIII).