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

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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Official URL: http://dx.doi.org/10.1016/S0040-4039(00)00689-4


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
Publication: Tetrahedron Letters
Publisher: Elsevier Science
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
URI: http://eprints.iisc.ac.in/id/eprint/31257

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