Chromophoric macrocycles from the oxidation of bis(aminofurazanylic) ethers of 1,2-diols

A series of chromophoric azofurazan-containing macrocycles 6a-c and 7a-d were synthesized from bis(aminofurazanylic) ethers of 1,2-diols 4a-d by dibromoisocyanurate oxidation.. The macrocycle closure is a result of N=N bond formation. An ion-binding ability of these compounds was tested. The macrocycles were characterized by NMR, MS, IR, and UV spectroscopy. The X-ray crystal structures of the macrocycles 6a, 7c, and linear counterpart 12 are reported. (C) 2004 Wiley Periodicals, Inc.