An alpha-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion

A novel sonication-promoted Barbier reaction putatively generated the title d species from the corresponding naphthotriazinylmethyl chloride and magnes ium in THF: its formal addition to a variety of carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the tr iazine moiety demasked the amine, thus defining a route to various phenylet hylamines (including the alkaloid 'mescaline'), or ethanolamines (in two ca ses), in excellent overall yields. (C) 2000 Elsevier Science Ltd. All right s reserved.