Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors |
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Authors: | Paul K. Bowyer David StC. Black Donald C. Craig |
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Affiliation: | a School of Agriculture and Wine, The University of Adelaide, Waite Campus, Glen Osmond SA 5064, Australia b School of Chemistry, The University of New South Wales, UNSW Sydney NSW 2052, Australia |
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Abstract: | Treatment of 3-(4-chlorophenyl)-7-hydroxymethyl-4,6-dimethoxyindole with 3-(4-chlorophenyl)-4,6-dimethoxyindole results in the generation of two geometrically isomeric diindolylmethanes in addition to a novel triindolyl oligomer, which has been structurally characterised. The 2,7′-diindolylmethanes were found to be unstable under Vilsmeier formylation conditions, thus hampering macrocyle precursor construction. In an alternate approach, the 3-(4-chlorophenyl)-4,6-dimethoxyindole-7-carbaldehyde was converted into the indolyl-pyrrolyl macrocycle precursor 5-(3-(4-chlorophenyl)-4,6-dimethoxyindole-2-ylmethyl)-4-ethyl-3-methylpyrrole-2,7-dicarbaldehyde, which was used to generate an unsymmetrical pentaaza macrocycle. |
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Keywords: | Indole Diindolylmethane Vilsmeier Macrocycle |
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