7167-81-9Relevant academic research and scientific papers
An efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoid alkaloids through phenolic Mannich reactions
Nguyen, Thanh Binh,Wang, Qian,Gueritte, Francoise
supporting information; experimental part, p. 7076 - 7079 (2012/01/05)
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 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.
