Abstract
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-dialkylaminoor 3-alkylamino-3-(1-amino-9,10-anthraquinon-2-yl)acrylate and 3-dialkylamino- or 3-alkylaminonaphthol[2,3-h]quinoline-2(1H), 7,12-trione (in ∼4: 1 ratio). Intramolecular cyclization of the resulting substituted ethyl acrylates results in the formation of 4-dialkylaminoor 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.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2327–2332, November, 1998.
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Barabanov, I.I., Fedenok, L.G. & Shvartsberg, M.S. Functionalized naphthol[2,3-h] quinoline-7,12-diones. Russ Chem Bull 47, 2256–2261 (1998). https://doi.org/10.1007/BF02494292
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DOI: https://doi.org/10.1007/BF02494292