I stumbled upon this paper when I'm trying to look at established protocol to synthesize one of the compounds (compound IIk) mentioned in the paper.
Studies on Aromatic Nitro Compounds. V. A Simple One-Pot Preparation of o-Aminoaroylnitriles from Some Aromatic Nitro Compounds
The paper described transformation of aromatic nitro compounds into o-aminoaroylnitriles by ethyl cyanoacetate in the presence of strong base. While the general scheme showed fused aromatics, this reaction also works for any electron-withdrawing (in addition to the nitro) containing single aromatics.
I have replicate the reaction for compound IIk and I was abled to purified the compound with yield consistent with what was described in the paper.
I have never seen this kind of transformation before, especially with ethyl cyanoacetate. The paper itself mentioned that the mechanism is unknown and I haven't found any subsequent papers that try to elucidate the mechanism.
Anyone has any idea how this reaction works?