Electrophilic Aromatic Substitution from a Peer-Reviewed Journal

Aromatic compounds have multiple double bonds so the compounds cannot undergo addition reactions. Therefore, they react by electrophilic aromatic substitution reactions. The aromaticity of the ring system is preserved. I found a peer-reviewed journal through Ebsco entitled, Reaction of N,N-Dimethylaniline with N-Cyanoazoles according to Electrophilic Aromatic Substitution Pattern, that discusses an electrophilic aromatic substitution reaction. This article was found in the Russian Journal of Organic Chemistry.


N-Cyanoazoles are highly reactive organic compounds. These compounds are important intermediate products that are involved in the synthesis of numerous derivatives containing an azole ring. N-cyanoazoles are capable of acting as electrophilic reagents in elctrophlic aromatic substitution reactions because of the high polarity of the cyano group.

This journal reported on the synthesis of some imines by electrophilic aromatic substituion of hydrogen in N,N-dimethylaniline by N-cyanoimidazole,  N-cyanobenzimidazole,  N-cyano-1,2,3-benzotriazole, and N-cyano-2-methylimidazoles. These N-cyanoazoles, Ia–Id, were prepared according to certain standard procedures.

They demonstrated that the previously listed N-cyanoazoles reacted with N,N-dimethylaniline in the presence  of anhydrous aluminum bromide to give para-substituted imines in good yields (65-74%). Nitrobenzene was found to be appropriate solvent for carrying out these reaction. reactions. The high polarity and dissolving
power of nitrobenzene ensure the homogeneity of the reaction mixture. However, nitrobenzene is not involved in the reaction because of the presence of a strong electron-withdrawing nitro group in its molecule.


Here is the picture of the substitution:

Reference:
Chunaev, A. O., Stepanov, E. A., & Purygin, P. P. (2010). Reaction of N, N-dimethylaniline with N-cyanoazoles according to electrophilic aromatic substitution pattern. Russian Journal of Organic Chemistry, 46(3), 459-460. doi:10.1134/S1070428010030309