Synthesis and utilisation of 2,7′-diindolylmethanes and a 2-(2-indolyl)pyrrolylmethane as macrocyclic precursors

Autor: Paul K. Bowyer, Donald C. Craig, David StC. Black
Rok vydání: 2005
Předmět:
Zdroj: Tetrahedron. 61:10781-10792
ISSN: 0040-4020
DOI: 10.1016/j.tet.2005.08.075
Popis: 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.
Databáze: OpenAIRE