Diaminomaleonitrile

Several nitrogen heterocycles, including imidazoles,¹⁻³ pyrazines,⁴ and diazepines,^(1, 3) have been prepared from diaminomaleonitrile (DAMN, 1), the tetramer of hydrogen cyanide.

The UV/Vis absorption spectra of the N,N′-disubstituted diaminomaleonitriles 1, 2 (Figure 1) and 3 (Figure S1 in the Supporting Information) in THF/H2O mixtures (1:1 v/v) show a charge transfer (CT) band of the push-pull diaminomaleonitrile electron system in the range of 280–350 nm.

Diaminomaleonitrile (DAMN), a stable tetramer of HCN, has long been renowned as a precursor for the formation of nucleobases.