title: Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides.
abstract: A synthesis of β-oxonitriles is reported via the generation of R(1)R(2)CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. (15)N- and (17)O-NMR data are reported for selected compounds.
authors.affiliation: Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, Vienna, A-1090, Austria. vittorio.pace@univie.ac.at.
authors.forename: Ashenafi Damtew
authors.initials: AD
authors.lastname: Mamuye
authors.forename: Laura
authors.initials: L
authors.lastname: Castoldi
authors.forename: Ugo
authors.initials: U
authors.lastname: Azzena
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Holzer
authors.forename: Vittorio
authors.initials: V
authors.lastname: Pace
mesh_terms: D000577:Amides / Q000737:chemistry*; D003489:Cyanoketone / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D009570:Nitriles; D003489:Cyanoketone