14H-Naphtho[1′,2′:5,6] pyrano[2,3-b]quinoline derivatives |
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Authors: | Giorgio Roma Aldo Ermili Alessandro Balbi |
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Abstract: | Reaction of (N-alkyl-N-phenyl)ethoxycarbonylacetamides with β-naphthol in the presence of phosphorus oxychloride afforded 1-oxo-3-(N-alkyl-N-phenyl)amino-1H-naphtho2,1-b]pyrans. These compounds underwent reaction with N,N-dimethylformamide-phosphorus oxychloride at 95° yielding a mixture of 14H-naphtho1′,2′:5,6]pyrano2,3-b]quinoline derivatives and 1-oxo-2-formyl-3-(N-alkyl-N-phenyl)amino-9-oxy-1H-phenalene. When the same reaction was performed at 140°, only 14-oxo-14H-naphtho1′,2′:5,6]pyrano2,3-b]quinoline was obtained in a very good yield. The structures of such compounds were demonstrated by spectral data and by chemical transformations. On the other hand, the expected formylation in the 2 position was achieved when 1-oxo-3-(N-alkyl-N-benzyl)amino-1H-naphtho2,1-b]pyrans reacted with N,N-dimethylformamide-phosphorus oxychloride. |
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