Cyano-aci-nitroacetate as a Safe Cyano (nitro) Methylation Reagent and its Synthetic Applications

Abstract

A practical, convenient, and safe cyano(nitro)methylation method was developed, in which cyano-aci-nitroacetate served as a synthetic equivalent of anionic nitroacetonitrile (NAN). Cyano-aci-nitroacetate, which possesses three different functional groups on the same carbon, reacts with ketones and aldehydes to afford polyfunctionalized nitriles, such as glutaronitriles, α-nitro-α, β-unsaturated nitriles and α-nitro-δ-keto nitrile. Furthermore, the obtained nitrile products can be used as precursors of polyfunctionalized heterocyclic compounds.