1296674-32-2Relevant 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.
Betti reaction of cyclic imines with naphthols and phenols - Preparation of new derivatives of Betti's bases
Cimarelli, Cristina,Fratoni, Davide,Mazzanti, Andrea,Palmieri, Gianni
experimental part, p. 2094 - 2100 (2011/05/16)
A large library of aminocycloalkylphenols and -naphthols is obtained by the Betti reaction between activated phenols and naphthols and five- and six-membered cyclic imines. Due to the formation of an intramolecular hydrogen bond in the transition state, the attack takes place regioselectively at the position adjacent to the hydroxy group of the aromatic compounds. X-ray crystallography and chirooptical methods (electronic circular dichroism) were used to ascertain the absolute configuration of two aminoalkylnaphthols obtained, after resolution of the corresponding racemates with (R,R)-tartaric acid. In addition, some aminoalkylnaphthols and-phenols were alkylated at the nitrogen atom to obtain N-methylated products in good yields. Copyright
