Synthesis and transformation of 6-aminomethyl derivatives of 7-hydroxy-2'-fluoroisoflavones

Makarenko, O., Bondarenko, S., Mrug, G., Frasinyuk, M. (2020). Synthesis and transformation of 6-aminomethyl derivatives of 7-hydroxy-2'-fluoroisoflavones. French-Ukrainian Journal of Chemistry, 8(2), 203–213. https://doi.org/10.17721/fujcV8I2P203-213

Mannich aminomethylation of 8-methyl-7-hydroxy-2'-fluoroisoflavones applying bis-(N,N-dimethylamino)methane afforded C-6 substituted N,N-dimethylaminomethyl derivatives. Subsequent acetylation of these compounds in acetic anhydride in the presence of potassium acetate provided access to the corresponding acetoxymethyl derivatives that were converted to hydroxymethyl- and alkoxymethyl-substituted 7-hydroxyisoflavonoids. Addition of 3-(N,N-dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one or 1,3-dimethyl-5-aminopyrazole with thermally generated ortho-quinone methides led to hetero-Diels–Alder or Michael adducts.