Synthesis of 1-arylmethyl-2-(cyanomethyl) aziridines and their ring transformation into methyl N-(2-cyanocyclopropyl) benzimidates

摘要

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.