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.
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.
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.
