title: Synthesis of 1-arylmethyl-2-(cyanomethyl)aziridines and their ring transformation into methyl N-(2-cyanocyclopropyl)benzimidates.
abstract: 1-Arylmethyl-2-(cyanomethyl)aziridines were prepared in high yields from the corresponding 2-(bromomethyl)aziridines upon treatment with potassium cyanide in DMSO. Ring opening of the aziridine moiety with N-chlorosuccinimide in CCl4 and subsequent treatment of the thus formed 4-chloro-3-(N-chloro-N-(alpha,alpha-dichlorobenzyl)amino)butanenitriles with sodium methoxide in methanol resulted in novel methyl N-(2-chloro-1-(cyanomethyl)ethyl)benzimidates, although in low yields. The latter gamma-chloro nitriles were smoothly converted into methyl N-(2-cyanocyclopropyl)benzimidates as precursors of biologically relevant beta-ACC derivatives through a 1,3-cyclization protocol by reaction with potassium tert-butoxide in THF.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Sven
authors.initials: S
authors.lastname: Mangelinckx
authors.forename: Evelien
authors.initials: E
authors.lastname: Persyn
authors.forename: Willem
authors.initials: W
authors.lastname: Van Brabandt
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis*; D007096:Imidoesters / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D001388:Aziridines; D007096:Imidoesters