A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis-Hillman adducts

Basavaiah, Deevi ; Lenin, Dandamudi V. ; Devendar, Badugu (2009) A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis-Hillman adducts Tetrahedron Letters, 50 (26). pp. 3538-3542. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2009.03.038

Abstract

3-Hydroxy-2-methylenealkanenitriles, the Baylis-Hillman alcohols, derived from various aldehydes and acrylonitrile, have been conveniently transformed into 3-arylidene(or alkylidene)piperidine-2,6-diones in an operationally simple one-pot multi-step process involving Johnson-Claisen (J-C) rearrangement, partial hydrolysis, and cyclization. Rearranged Baylis-Hillman alcohols, (E)-2-hydroxymethyl-3-arylprop-2-enenitriles, have been converted into 4-aryl-3-methylidenepiperidine-2,6-diones in a similar reaction sequence. 4-Aryl-3,5-dimethylidenepiperidine-2,6-dione derivatives have been synthesized from Baylis-Hillman compounds, 3-aryl-4-cyano-2-methoxycarbonylpenta-1,4-dienes, obtained via the Baylis-Hillman reaction of methyl (2Z)-2-(bromomethyl)-3-arylprop-2-enoates with acrylonitrile, in a one-pot process.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Baylis-Hillman Alcohols; Johnson-Claisen Rearrangement; Partial Hydrolysis; Cyclization; Piperidine-2,6-diones; DABCO
ID Code:3927
Deposited On:18 Oct 2010 09:25
Last Modified:18 Oct 2010 09:25

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