Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications.

Hydroxy-substituted tetrachlorodibenzo[][1,4]dioxin and tetrachlorodibenzo[]furans have been synthesized using 3,4-dichloroanisole, 2,3,6-trichlorophenol and 4,5-dichlorocatechol as starting materials and electrophilic and/or nucleophilic aromatic substitution reactions for the assembly of the dibenzo[][1,4]dioxin and dibenzo[]furan systems. The thus-obtained phenolic compounds were then alkylated with N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde)-protected 3-bromopropan-1-amine to give the corresponding N-Dde protected 3-aminopropoxy-substituted tetrachlorodibenzo[][1,4]dioxin and tetrachlorodibenzo[]furans, respectively. Hydrazinolysis-mediated Dde removal from the former compound provided the corresponding amino-substituted dioxin, which was coupled to carboxy-substituted magnetic beads affording magnetic beads coated by the amino-substituted dioxin.