Collect. Czech. Chem. Commun. 1980, 45, 2329-2333

Reactions of pyridyl isothiocyanates with diazoalkanes and azoimide

Miroslav Marchalín and Augustin Martvoň

Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava


Reaction of 2-, 3- and 4-pyridyl isothiocyanates with diazomethane or diazoethane afforded the corresponding 5-(pyridyl substituted)amino-1,2,3-thiadiazoles or 5-(pyridyl substituted)-amino-4-methyl-1,2,3-thiadiazoles; reaction with azoimide gave 5-(pyridyl substituted)amino-1,2,3,4-thiatriazoles and 5-(2-pyridylamino)tetrazole, which underwent a thermal rearrangement to yield 1-(2-pyridyl)-5-aminotetrazole. The synthesized derivatives are characterized by IR, UV, mass and 1H-NMR spectra.