Some condensations of methyl 4-acetylphenylcarbamate |
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Authors: | A V Velikorodov N M Imasheva A K Kuanchalieva O Yu Poddubnyi |
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Institution: | 1.Astrakhan State University,Astrakhan,Russia |
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Abstract: | Condensation of methyl 4-acetylphenylcarbamate with isatin in the presence of diethylamine afforded methyl 4-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetyl]phenylcarbamate which was converted into the corresponding chalcone on heating in glacial acetic acid in
the presence of hydrochloric acid. 1,3-Dipolar cycloaddition to that chalcone of azomethine ylide generated from 2-phenacylisoquinolinium
bromide by the action of triethylamine gave methyl 4-(3′-benzoyl-2-oxo-1′,2,2′,3,3′,10b′-hexahydro-1H-spiro-indole-3,1′-pyrrolo1,2-a]isoquinolin]-2′-ylcarbonyl)phenylcarbamate. Condensation of 2-hydroxy- and 2,4-dihydroxybenzaldehydes with methyl 4-acetylphenylcarbamate
in the presence of gaseous hydrogen chloride resulted in the formation of chromenium salts with a methoxycarbonylaminophenyl
fragment on the C2 atom in the heteroring. |
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