Synthesis, characterization, and structural investigations of 1-amino-3-substituted-1,2,3-triazolium salts, and a new route to 1-substituted-1,2,3-triazoles

Abstract

Quarternary salts based upon 3-alkyl substituted 1-amino-1,2,3-triazolium cations (alkyl = methyl, ethyl, nypropyl, 2-propenyl, and n-butyl) have been synthesized and characterized by vibrational spectra, multinuclear NMR, elemental analysis, and DSC studies. Subsequent diazotization of these salts results in the exclusive formation of 1-alkyl-1,2,3-triazoles. Single crystal X-ray studies were carried out for 1-amino-3-methyl-1,2,3-triazolium iodide, 1-amino-3-ethyl-1,2,3-triazolium bromide, 1-amino-3-n-propyl-1,2,3-triazolium bromide, and 1-amino-3-n-butyl-1,2,3-triazolium bromide as well as the starting heterocycle, 1-amino-1,2,3-triazole, and all of the structures are discussed.