The preparation of a-monosubstituted indoles by (a) the Madelung reaction,(b) o-nitrobeneyl ketone reduction, and (c) o, p-dinitrostyrene reduction was explored. The Madelung reaction is limited to use on those toluidides which do not have double bonds or active hydrogens present. Toluidides having tertiary benzylamine groups can be used. o-Kitrobenzyl ketone preparations were attempted by the arylation of p-keto esters with o-fluoronitrobenzene. ...
