- Electrophilic substitution of dimethyl 1 -methylcarbazole-2,3-dicarboxylate: Synthesis of new b-fused carbazoles as potential antitumor agents
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1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine- or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.
- Haider, Norbert,Marian, Brigitte,Nagel, Thomas,Tarnai, Markus,Trapper, Katharina
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p. 1965 - 1974
(2015/01/08)
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- The Mechanism of Formation of 3H,9H-Pyranoindol-3-ones from 3-Indolalkanoic Acids
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The mechanism of the formation of 1-methyl-3H,9H-pyranoindol-3-one (4) from the corresponding 3-indolacetic acid 1 is discussed.The suggested mechanism is substantiated by the isolation of a stable intermediate 2 and its transformations in the presence of acetic anhydride and/or Lewis acids. Key Words: 3H,9H-Pyranoindole derivative / Indole derivatives
- Medio-Simon, Mercedes,Erfanian-Abdoust, Houshang,Pindur, Ulf
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p. 601 - 602
(2007/10/02)
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- Synthesis of the Carbazole Alkaloids Carbazomycin A and B and Hyellazole
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The first synthesis of carbazomycins A and B (1) is described; the route involves Diels-Alder reaction of 1-methylpyranoindol-3-one with ethyl 3-trimethylsilylpropynoate followed by functional group interconversions; the marine alkaloid hyellazole
- Moody, Christopher J.,Shah, Pritom
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p. 376 - 377
(2007/10/02)
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