Quinone-Amine Reactions, IX: Reactions Between 1,4-Naphthoquinones and N-Substituted Ethylenediamines

Article abstract of DOI:10.1002/ardp.19843170903

N-Alkylethylenediamines 7a/b react with 1,4-naphthoquinones 6 to give 4-alkylbenzoquinoxalinones 3a/b, which are not accessible by alkylation of unsubstituted benzoquinoxalinones 1.On the other hand, N-arylethylenediamines 7c/d yield arylamino(ethylamino)-1,4-naphthoquinones 10c/d.Intramolecular catalysis of the proton transfer explains the fact that the reaction proceeds considerably slower than that of unsubstituted ethylenediamine (5).