An a-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion
Date
2012-11-20
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Abstract
A novel sonication-promoted Barbier reaction putatively generated the titled species from the corre-
sponding naphthotriazinylmethyl chloride and magnesium in THF: its formal addition to a variety of
carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the triazine
moiety demasked the amine, thus de®ning a route to various phenylethylamines (including the alkaloid
`mescaline'), or ethanolamines (in two cases), in excellent overall yields. # 2000 Elsevier Science Ltd. All
rights reserved.
Description
A novel sonication-promoted Barbier reaction putatively generated the titled species from the corre-
sponding naphthotriazinylmethyl chloride and magnesium in THF: its formal addition to a variety of
carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the triazine
moiety demasked the amine, thus de®ning a route to various phenylethylamines (including the alkaloid
`mescaline'), or ethanolamines (in two cases), in excellent overall yields. # 2000 Elsevier Science Ltd. All
rights reserved.
Keywords
Keywords: alkaloids; a-aminomethyl carbanion; Barbier reaction; mescaline; naphthotriazine; phenylethylamine; ultra- soun