Functionalized naphtho[2,3-h]quinoline-7,12-diones

The addition of secondary and primary amines to ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate affords an easily separable mixture of the corresponding ethyl 3-dialkylamino- or 3-alkylamino-3-(1-amino-9, 10-anthraquinon-2-yl)acrylate and 3-dialkylamino- or 3-alkylaminonaphtho[2,3-h]quinoline-2(1H),7,12-trione (in similar to 4: 1 ratio). Intramolecular cyclization of the resulting substituted ethyl acrylates results in the formation of 4-dialkylamino- or 4-alkylamino-2-chlorinated pyridine rings. Subsequent nucleophilic substitution of the chlorine atom gives 2-functionalized 4-dialkylamino- or 4-alkylaminonaphtho[2,3-h]quinoline-7,12-diones.