Abstract 3-[(2-Imidazolyl, benzimidazolyl or benzoxazolyl) alkyl] indoles 2a-h were synthesized by cyclizing the carboxylic group of (3-indolyl) alkanoic acids 1 with ethylenediamine, o-phenylenediamine or o-aminophenol, respectively. Reaction of 1 with p- aminoacetophenone or aryl-substituted thiosemicarbazones yielded N-(4-acetylphenyl)-(2 or 4)-(indol-3-yl) alkylcarboxamides 3a-b or 1-arylidene 4-[2-(indol-3-yl)(acetyl or ...