Synthesis of Selectively Substituted Lipocyclopolyamines

A general synthetic strategy for the preparation of polyazamacrocycles containing long aliphatic chains is reported. These compounds are 22‐ or 24‐membered hexaazamacrocycles incorporating two diethylenetriamine subunits (H2NCH2CH2NHCH2CH2NH2) linked together either by two CH2CH2OCH2CH2 (see 4–6), two tetramethylene (see 7), or two pentamethylene (see 8) fragments. Whereas for compound 4, one of the centrally located amine functionalities of the triamine subunit bears a hexadecyl chain, for compound 5, two of such chains are centrally attached to both subunits. In macrocycles 6–8, all six amino functionalities bear hexadecyl chains. Compounds 4–8 are potential candidates for the construction of selective chemical sensors such as specific electrodes for adenosine mono‐, di‐, and tri‐phosphate. They may also be used for nucleoside polyphosphates extraction and/or transport.