SYNTHESIS AND CHARACTERIZATION OF VARIOUS UNSUBSTITUTED AND MONO-N-SUBSTITUTED TETRAAZAMACROCYCLES

Syntheses of tetraazamacrocycles have been carried out by using p-tolu enesulfonyl chloride as protective group. The [14(ane) N4] and [15(ane ) N4] were also obtained by the template synthesis. Mono-N-functionali zation ion of tetraazamacrocycles was accomplished by reaction of a fi vefold excess of the free macrocycles with 1 equivalent of a suitable alkylating or arylating reagent. The key point of the synthesis lies i n the use of an excess of the macrocycle over the substituting reactan ts to reduce the formation of polysubstituted derivatives, and in the easy separation of the excess of unreacted macrocycle. All the product s were characterized on the basis of spectral studies (H-1 and C-13 NM R, including 2D NMR and NOE difference studies) and mass spectrometry.