One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives

Andrey N. Vorobiov; Pavel N. Gaponik; Petr T. Petrov; Oleg A. Ivashkevich

doi:10.1055/s-2006-926403

PAPER

One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives

Andrey N. Vorobiov*^a, Pavel N. Gaponik^b, Petr T. Petrov^a, Oleg A. Ivashkevich^b
^a Scientific Pharmaceutical Center, RUE Belmedpreparaty, Fabritsiusa Str. 30, Minsk 220007, Belarus
^b Research Institute for Physico-Chemical Problems, Belarusian State University, Leningradskaya Str. 14, Minsk 220050, Belarus
Fax: +375(17)2293926; e-Mail: azole@bsu.by;

Abstract

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Abstract

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.

Key words

5-aminotetrazoles - tetrazolium salts - heterocycles - tandem reactions - regioselectivity

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