Synfacts 2009(7): 0723-0723  
DOI: 10.1055/s-0029-1217316
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Cycloaddition Route to 5-Aminotriazoles

Contributor(s): Victor Snieckus, Timothy Hurst
N. T. Pokhodylo, V. S. Matiychuk, M. D. Obushak*
Ivan Franko National University of Lviv, Ukraine
Further Information

Publication History

Publication Date:
22 June 2009 (online)


The regioselective synthesis of
5-aminotriazoles 3 from aryl azides 1 and cyano-acetyl pyrroles and indoles 2 is reported. The key to the regioselectivity is the presence of the electron-rich heteroaryl (R²) group, which disfavors cyclization at the carbonyl position (path B), leading instead to attack on the nitrile (path A) giving rise to the observed products. Electron-donating, -neutral and -withdrawing aryl substituents are tolerated in the reaction and high yields were obtained for all examined cases.