188557-88-2Relevant academic research and scientific papers
One-pot formation of aza-enolates from secondary amines and condensation to esters and alkyl bromides
Chevalley, Alice,Férézou, Jean-Pierre
experimental part, p. 5882 - 5889 (2012/09/11)
Starting from commercial secondary amines, a one-pot procedure allows a direct access to enaminones through a one-pot deprotonation/oxidation/in situ re-deprotonation/acylation sequence without intermediate isolation of the intermediate Schiff base or its corresponding enamine tautomer. An alternative one-pot sequence involving a similar oxidation step followed by one or two alkylation steps yields, after acidic work-up, functionalized ketones directly from the parent amine. This process has been applied to an expeditious synthesis of the male aggregation pheromone of the cereal leaf beetle Oulema melanopus.
A new protocol for the synthesis of α',β'-unsaturated 1,3-diketones
Dalpozzo, Renato,De Nino, Antonio,Iantorno, Emma,Bartoli, Giuseppe,Bosco, Marcella,Sambri, Letizia
, p. 2585 - 2590 (2007/10/03)
Dianions of α'-(trimethylsilyl)enaminones can be used as Peterson reagents in the reaction with aldehydes and ketones, to obtain α',β'-unsaturated enaminones or 1,3-diketones with regio and stereocontrol of the new double bond.
An efficient, scaleable procedure for the conversion of esters to isoxazoles
Bunnelle,Singam,Narayanan,Bradshaw,Liou
, p. 439 - 442 (2007/10/03)
A concise, regiocontrolled route to isoxazoles, based on the condensation of an ester with a metallated imine, has been developed. The intermediate vinylogous amides react smoothly with hydroxylamine to provide, after dehydration, substituted isoxazoles. The method has been used for the multi-kilo scale preparation of ABT-418, a novel cholinergic channel activator.
