Chandrasekhar, Sosale and Sridhar, Malayalam (2000) An alpha-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion. In: Tetrahedron Letters, 41 (23). pp. 4685-4688.
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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 defining a route to various phenylethylamines (including the alkaloid 'mescaline'), or ethanolamines (in two cases), in excellent overall yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Elsevier Science.|
|Keywords:||Alkaloids;α-aminomethylcarbanion;Barbier reaction; mescaline;naphthotriazine;phenylethylamine;ultrasound.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||25 Aug 2010 06:21|
|Last Modified:||19 Sep 2010 06:13|
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