119930-89-1Relevant academic research and scientific papers
A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis-Hillman adducts
Basavaiah, Deevi,Lenin, Dandamudi V.,Devendar, Badugu
experimental part, p. 3538 - 3542 (2009/10/26)
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.
New Phosphonium Ylides by Functionalization of Triphenylphosphoranylideneacetamide
Wanner, Martin J.,Koomen, Gerrit-Jan
, p. 1513 - 1516 (2007/10/02)
Triphenylphosphoranylideneacetamide undergoes Michael reactions with several acceptors, giving rise, apart from the normal Michael adducts, to the formation of different products like glutarimide ylides and stabilized iminophosphoranes.Wittig reactions with these new ylides lead to a variety of α,β-unsaturated carbonyl compounds. Key Words: Stabilized phosphonium ylides, Wittig reaction, Michael reaction, Glutarimides.
2-Substituted Glutarimides via Preformed Wittig Reagents
Wanner, M. J.,Koomen, G. J.
, p. 325 - 327 (2007/10/02)
Triphenylphosphoranylideneacetamide (1) reacts with some Michael-acceptors to give crystalline 2-triphenylphosphoranylidene glutarimides.The Wittig reaction of 2 with several aldehydes in refluxing 1,2-dichloroethane affords the corresponding 2-alkylidene
