diazaindenes (azaindoles)-IV. Oxidation of 1,5- and 1,7-diazaindenes and a novel route to 3-substituted diazaindenes

Article abstract of DOI:10.1016/S0040-4020(01)97027-9

Treatment of certain 1,5- and 1,7-diazaindenes with a small molar excess of hydrogen peroxide in acetic acid causes opening of the pyrrole ring with loss of the 2-C atom to give aminopyridyl ketones or aminopyridine carboxylic acids. The former have been used as intermediates in the synthesis of 3-substituted diazaindenes by reaction with dimethylsulphonium methylide. Stable iodine complexes with 1,5-diazaindenes may be formed: 6-(4-aminopyrid-3-yl)-6-oxohexanoic acid gave 4-(1-methyl-1,5-diazainden-3-yl)butanoic acid.