Some reactions of 6,8-dimethoxypyrrolo[3,2,1-hi]indoles

Two 6,8-dimethoxypyrrolo[3,2,1-hi]indole carboxylic esters were hydrolyzed and decarboxylated. In an investigation of their electrophilic substitutions, some pyrroloindoles were formylated using the Vilsmeier reagent, and acylated with oxalyl chloride followed by quenching with dimethylamine to give the glyoxylic amides. The electrophilic substitutions occur at the C2 or C4 position (α to the nitrogen atom) rather than the C1 or C5 position (β to the nitrogen atom). Four of the formyl and acyl products were reduced to the corresponding methanol derivatives. These compounds reacted on treatment with a range of acids, but pure products could not be separated from the complex mixtures.