Studies in the synthesis of furocoumarins. Part 29: Synthesis of aminomethyl psoralen and angelicin derivatives as potential photo-chemotherapeutic agents.

Bromination of 2,7-dimethylfuro[2,3-h]benzopyran-5[H]-one (1a) and 2,5-dimethylfuro[3,2-g]benzopyran-7[H]-one (2a) with N-bromosuccinimide gave 2-bromomethyl-7-methylfuro[2,3-h]benzopyran-5[H]-one (1b) and 2-bromomethyl-5-methylfuro[3,2-g]benzopyran-7[H]-one (2b), respectively. The derivatives 1b and 2b were converted to 2-aminomethyl derivatives 1 c-h and 2 c-f by treatment with the appropriate secondary amine. The structures of 2-bromomethyl derivatives 1b and 2b have been confirmed by 13C-NMR spectra.