Programmed Formation of HCN Oligomers through Organosulfur Catalysis

An efficient, inexpensive, and reliable synthesis of diaminomaleonitrile (DAMN, 1) is described starting from readily available acetone cyanohydrin as the source of hydrogen cyanide (HCN). Diaminomaleonitrile (DAMN) is known to be an important intermediate in heterocyclic and medicinal chemistry as well as being a possible precursor for the origin of life's hypothesis within prebiotic chemistry. The mechanism of its formation through organosulfur catalysis has been investigated by electrospray ionization mass spectrometry (ESI-MS) using two newly synthesized cationic marker molecules as a tool that allows for sensitive detection. As a result, the proposed mechanism of a thiocyanate-mediated synthesis of the HCN tetramer DAMN starting from organic disulfides was confirmed.

Automated summary

An efficient, inexpensive, and reliable synthesis of diaminomaleonitrile (DAMN) starting from acetone cyanohydrin as the source of hydrogen cyanide (HCN) is described. The formation mechanism of DAMN through organosulfur catalysis was investigated using electrospray ionization mass spectrometry (ESI-MS) with newly synthesized cationic marker molecules, confirming the proposed thiocyanate-mediated synthesis of the HCN tetramer DAMN starting from organic disulfides.