Functionalized naphthol[2,3-h] quinoline-7,12-diones |
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Authors: | I. I. Barabanov L. G. Fedenok M. S. Shvartsberg |
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Affiliation: | (1) Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 ul. Institutskaya, 630090 Novosibirsk, Russian Federation |
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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. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2327–2332, November, 1998. |
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Keywords: | ethyl (1-amino-9,10-anthraquinon-2-yl)propynoate, addition of amines, intramolecular cyclization 4-dialkylamino-, 4-alkylamino-, 3-dialkylamino-, and 3-alkylaminonaphtho[2,3-h]quinoline-2(1H), 7,12-triones 2-substituted 4-dialkylamino- and 4-alkylaminonaphthol[2,3-h]quinoline-7,12-diones |
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