An Efficient One??Step Synthesis of Piperidin??2??yl and Pyrrolidin??2??yl Flavonoid Alkaloids through Phenolic Mannich Reactions

TB Nguyen, Q Wang, F Guéritte

Index: Nguyen, Thanh Binh; Wang, Qian; Gueritte, Francoise European Journal of Organic Chemistry, 2011 , # 35 p. 7076 - 7079

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Citation Number: 7

Abstract

Abstract An 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 H 2 O/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 ...