Efficient syntheses of macrocycles ranging from 22-28 atoms through spontaneous dimerization to yield bis-hydrazones.

Acid treatment of a triazine displaying both a tethered acetal and BOC-protected hydrazine group leads to spontaneous condensation to yield macrocyclic dimers in excellent yields and purity. The bis-triazinyl hydrazones that form are characterized by H-NMR, C-NMR, H-COSY spectroscopy, X-ray diffraction, and mass spectrometry. By varying the length of the tether-the condensation product of an amino acid and amino acetal-rings comprising 22-28 atoms can be accessed.