- Reactions of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates. Synthesis of methyl isoxazolo[5,4-a]carbazole-3-carboxylates
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The reaction of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates (1a-e) with hydroxylamine hydrochloride in alcoholic KOH afforded 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles (2a-e), and in acetic acid methyl isoxazolo[5,4-a]carbazole-3-carboxylates (3a-e). Ketoesters 1a-e with urea and thiourea under acidic conditions yielded a mixture of the respective 1-hydroxycarbazoles (6a-e) and 2,3,4,9-tetrahydro-1H-carbazol-1-ones (7a-e), but under basic conditions the respective 1-carbimido-and 1-thiocarbimido-2,3,4,9- tetrahydro-1H-carbazoles (8a-e and 9a-e) were formed. Plausible mechanisms are proposed.
- Martin, Arputharaj Ebenezer,Prasad, Karnam Jayarampillai Rajendra
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p. 653 - 656
(2008/09/17)
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- Attempted synthesis of substituted carbazoles from 1 -oxo-1,2,3,4- tetrahydro-carbazoles and 1-hydroxyimino-1,2,3,4-tetrahydrocarbazoles
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The reaction of 1-oxo-1,2,3,4-tetrahydrocarbazoles 1 with vinyl acetate in presence of alcoholic KOH affords hitherto unknown 7-methyl-1-oxo-2-(3′- methyl propan-1′-al)-1,2,3,4-tetrahydrocarbazole 2. Similarly, the reaction of 1-hydroxyimino-1,2,3,4-tetrahydrocarbazoles 3 with vinyl acetate in the presence of p-toulenesulphonic acid results in the formation of a new compound viz., 2-acetoxy-1,2,3,3a,4,5-hexahydropyrrolo[3,4-a]carbazole 4. All the compounds have been characterized by IR, NMR and mass spectra and elemental analysis.
- Danish, I. Antony,Prasad, K. J. Rajendra
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p. 540 - 545
(2007/10/03)
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