Nguyen, Thanh BinhWang, QianGueritte, Françoise2012-06-122012-06-122012-06-12201110.1002/ejoc.201101312https://infoscience.epfl.ch/handle/20.500.14299/81594WOS:000297466000006An efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoid alkaloids was achieved in good to excellent yields by a highly regioselective phenolic Mannich reaction of chrysin with cyclic imines or iminium salts. Performing the reaction in a mixture of H2O/THF in the absence of an external reagent afforded the C-6 alkylated product exclusively. The same reaction in water in the presence of NaOH provided the C-8 alkylated flavonoid as a major product. The reaction has been successfully extended to simple phenols.AlkaloidsMannich reactionIminesNatural productsRegioselectivityFriedel-Crafts ReactionsSolvent-FreeBuchenavia-CapitataBiological-ActivityAmino-AcidsBiosynthesis3,4-DihydroisoquinolineInhibitorsNicotineAn Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids through Phenolic Mannich Reactionstext::journal::journal article::research article