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

M.V. MIRÍFICO; J. A. CARAM; O. E. PIRO; E. J. VASINI

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

Wiley

Año: 2007 vol. 20 p. 1081 - 1087

0894-3230

The first nucleophilic addition of an inorganic nucleophile (cyanide) to the activated, rigid, a-diazomethine groups of a 1,2,5-thiadiazole 1,1-dioxide is reported here. An a-amino nitrile and a bis a-aminonitrile 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—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 a-amino nitrile derivative.