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

✍ Scribed by Sosale Chandrasekhar; Malayalam Sridhar

• Book ID: 104210413
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 111 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00689-4

✦ Synopsis

A novel sonication-promoted Barbier reaction putatively generated the titled species from the corresponding 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.