131202-39-6Relevant 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
body text, 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.
Synthesis of stereochemically defined (E)-cinnamyl alcohol derivatives from the Baylis-Hillman adducts
Shik Kim, Hyoung,Yi Kim, Tae,Young Lee, Ka,Mi Chung, Yun,Jung Lee, Hong,Nyoung Kim, Jae
, p. 2613 - 2616 (2007/10/03)
The reaction of the Baylis-Hillman adducts 1a-g and trifluoroacetic acid at 30-70°C gave the rearranged cinnamyl alcohols 2a-g stereoselectively in moderate yields. (C) 2000 Elsevier Science Ltd.
Applications of the baylis-hillman adducts in organic synthesis: A facile synthesis of [E]-α-cyanocinnamyl alcohols and [E]-α-cyanocinnamic aldehydes
Basavaiah, Deevi,Kumaragurubaran, Nagaswamy,Padmaja, Kisari
, p. 1630 - 1632 (2007/10/03)
Aqueous sulfuric acid mediated transformation of the Baylis-Hillman adducts, i.e. 3-aryl-3-hydroxy-2-methylenepropanenitriles, into [E]-α- cyanocinnamyl alcohols and subsequent oxidation with PCC leading to the formation of stereochemically pure [E]-α-cya
A new and efficient method for the isomerization of secondary functional allylic alcohols into their primary isomers
Beltaief, Imen,Hbaieb, Souhaira,Besbes, Rafaa,Amri, Hassen,Villieras, Monique,Villieras, Jean
, p. 1765 - 1768 (2007/10/03)
The first efficient tandem: 'bromination-formylation-hydrolysis' for the 1,3-transposition of acyclic allylic alcohols 1 and 2 bearing a nitrile and an ester group is reported.
New efficient synthesis of 3-substituted 2-cyano allylic alcohols
Hbaieb,Ben Ayed,Amri
, p. 2825 - 2832 (2007/10/03)
An efficient tandem 'bromination-formylation-hydrolysis' mediated conversion of available 2-(1-hydroxy alkyl) acrylonitriles I to their corresponding 3-substituted 2-cyano allylic alcohols 2 is described.
A simple route to 3-substituted 2-cyano allylic alcohols
Aiai, Mouna,Baudy-Floc'h, Michèle,Robert, Albert,Le Grel, Philippe
, p. 403 - 406 (2007/10/03)
The first original and simple route to 3-substituted 2-cyano allylic alcohols with very good yields is described. The epoxide function in the key step acts as a protecting group during the synthesis of these allylic alcohols.
