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Unsaturated crown-containing and methoxy-substituted styrylheterocycles of the 4-pyridine and 4-quinoline series were synthesized by condensation of methyl-substituted heterocycles with benzaldehydes in the presence of base. Synthesis of 18-crown-6-containing styrylpyridine by condensation of the reagents in Ac2O was developed. A simple and efficient method for the preparation of crown-containing and methoxy-substituted hetarylphenylacetylenes by the bromination followed by dehydrobromination reactions of the corresponding styrylheterocycles. Complex formation of styrylheterocycles and hetarylphenylacetylenes with macroheterocyclic compounds (cavitands) – b-cyclodextrins and cucurbit[7]uril – was studied by electronic and 1H NMR spectroscopy methods. It was established pseudorotaxane structure and stability constants of the inclusive complexes of the “host–guest” type.