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The reaction of 2-substituted malonaldehydes (7) with aromatic 1,2-diamines (5 or 6) in ethanol/acetic acid (10:1) leads to 6,13-disubstituted 1,4,8,11 -tetraaza[14]annulene derivatives (8 or 9) even in the absence of coordinating metal cations ("non-template" synthesis), and not to 3-substituted 1,5-benzodiazepines such as 4. Cobalt(II), nickel(II), and copper(II) complexes of the macrocyclic chelate ligands 8 and 9 have been observed by subsequent metallization with the corresponding acetates in N,N-dimethylformamide. The structures of 8-11 have been assigned mainly by their mass spectra.

zeitschrift für naturforschung b

Synthesen mit aliphatischen Dialdehyden, XXVII [1] Eine „non-template“-Synthese zur Darstellung metallfreier 1.4.8.11-Tetraaza [14] annulen-Derivate / Syntheses with Aliphatic Dialdehydes, XXVII [1] A Non-Template Synthesis for the Preparation of Metal-Free 1,4,8,11-Tetraaza[14]annulene Derivatives