A novel facile route for the introduction of 5-amino and 5-alkylamino substituents
into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was
obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive
ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles
were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence
of the nature of aryl substituents and reaction conditions on the regioselectivity
of the intramolecular cyclization of intermediate guanyl azides is revealed.
5-aminotetrazoles - tetrazolium salts - heterocycles - tandem reactions - regioselectivity
