Porphyrazines with tosylamine functional groups

Metal-free (3b) and metallo-porphyrazines (3a, 3c, 3d) (M=Mg, Ni and Co) carrying eight functional tosylaminoethylthia-groups on peripheral positions have been synthesised for the first time from cyclotetramerization of 1,2-bis(2-tosylaminoethylthia)maleonitrile (2) in the presence of magnesium propoxide; the metal-free derivative 3b was obtained by treatment of 3a with trifluoroacetic acid and it was further converted into Co(II) (3c) and Ni(II) (3d) derivatives by using acetate salts of corresponding metal ions. The reactivity of tosylamino-groups was verified by its alkylation to yield octakis[(tosyl)(hexyl)amino- ethylthia]porphyrazinatomagnesium(II) (4a).The new compounds were characterised by elemental analysis, IR, NMR and UV-vis spectra.