N-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthyl)acetamide (1) reacts with aromatic amines to give the 2-acylamino-3-arylamino-1,4-naphthoquinones. Whereas with the substituted o-phenylenediamines, o-aminophenols, o-aminobenzenethiols and 2-amino-3-hydroxy pyridine it gives angular heterocyclic compounds. A common reaction path is suggested

N-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthyl)acetamide reacts with aromatic amines to produce 2-acylamino-3-arylamino-1,4-naphthoquinones

Paper

Angular Heterocycles. The Reaction of N-(3-Chloro-1,4-dihydro-1,4-dioxo-2-naphthyl)acetamide with Isoelectric Bifunctional Aromatic Amines

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