Alkaloid quindoline, its structural analogues and δ-carbolines were obtained through the Cadogan reaction using DPPE under solvent-free conditions as a key stage of the synthesis.Various o-nitroarylpyridines prepared by one-pot synthesis from nitroacetophenones, methyl orthoformate and acetoacetic ester enamine were used as starting materials for the preparation of δ-carbolines. 2-Aryl-3-nitro-5,6,7,8-tetrahydroquinolines obtained by reacting 2-hydroxymethylenecyclohexanone with nitroacetophenones enamines were used for the synthesis of quindoline and its structural analogs. A relationship between the structure and optical properties of the synthesized compounds was found.