Studies on the chemical constituents of rutaceous plants. XLIX. Development of a versatile method for the synthesis of antitumor-active benzo[c]phenanthridine alkaloids. (1). Preparation of various 2,4-bisaryl-4-oxobutyronitriles and 2,4-bisaryl-4-oxobutyramides

Article abstract of DOI:10.1248/cpb.31.3024

For the sake of establishment of a versatile synthetic method for benzo[c]phenanthridine alkaloids, improvement of the Robinson synthetic method was examined. Thirteen chalcones (7a-m) were prepared by condensation of two acetophenone derivatives (15 and 16) with eleven benzaldehyde derivatives (19a-k) as fundamental starting materials. Hydrocyanation of these chalcones (7a-1) except one (7m) gave the corresponding 2,4-bisaryl-4-oxobutyronitriles (8a-1). Eleven 2,4-bisaryl-4-oxobutyramides (9a-k) were also prepared.