Synthesis of an α-amino nitrile and a bis α-amino nitrile derivative of thiadiazole: reaction mechanism.

The first nucleophilic addition of an inorganic nucleophile (cyanide) to the activated, rigid, α-diazomethine groups of a 1,2,5-thiadiazole 1,1-dioxide is reported here. An α-amino nitrile and a bis α-amino nitrile derivatives were obtained in good yields (62 and 98%, respectively) and characterized by spectroscopic, analytical, and single crystal X-ray diffraction techniques. The course of the reaction, followed by cyclic voltammetry (CV), showed that cyanide adds to only one of the two C&dbond;N double bonds of the thiadiazole, forming an anion from which an N-methyl derivative was obtained. Adequate concentrations of cyanide and methyl iodide (MeI) produced directly the bis α-amino nitrile derivative. Copyright © 2007 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]