Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles
A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.
A Pd-catalyzed asymmetric allylic substitution cascade: Via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans
A Pd-catalyzed asymmetric allylic substitution cascade of allylic meso-dicarbonates with 3-oxo-nitriles has been developed for the synthesis of chiral bicyclic dihydrofurans bearing two vicinal carbon stereocenters. The reaction proceeds via an asymmetric desymmetrization process with the desired products being obtained in high yields and with up to 97% ee. The reaction was performed on a gram-scale and the corresponding bicyclic dihydrofurans could undergo several transformations. The methodology provides an efficient synthetic route to biologically active chiral bicyclic dihydrofurans derivatives.
Arylpropanolamines incorporating an antioxidant function as neuroprotective agents
A series of arylpropanolamines containing dipyrrolidinylpyrimidines as an antioxidant function have been synthesized and evaluated as dual function neuroprotective agents. Their in vitro efficacy as sodium channel blocking agents and antioxidants has been evaluated and compared with those of the ethanolamine derivative (1), which has been shown to be neuroprotective in a rat model of stroke. The ability of the present compounds to displace 3H-BTX toxin from sodium-ion channels in a rat brain membrane fraction was shown to be largely independent of the substituents on the aryl ring, which suggests that this activity may be mainly associated with the aminopyrimidine moiety. Structure-activity relationships for antioxidant efficacy were less clear, but the unsymmetrical pyrimidines were consistently more active than their symmetrical isomers. A brief theoretical investigation of this observation is reported.
Joubran, Lida,Jackson, W. Roy,Campi, Eva M.,Robinson, Andrea J.,Wells, Bradley A.,Godfrey, Peter D.,Callaway, Jennifer K.,Jarrott, Bevyn
p. 597 - 605
(2007/10/03)
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