Sequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert -butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N -alkoxyindoles. In related reactions, using sodium tert -pentoxide as the base with or without in situ addition of an electrophile afforded N -alkoxy- and N -hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p -tosyl chloride, and acetic anhydride afforded moderate yields of the respective N -methoxy-, N -tosyloxy, and N -acetoxyindoles, while methyl iodide, benzyl bromide, and 1-bromohexane failed to form alkylated products using sodium tert -pentoxide as the base.