Synthesis of N,N-Disubstituted 3-Amino-1,2,4-triazoles

Alan R. Katritzky; Boris V. Rogovoy; Vladimir Y. Vvedensky; Katherine Kovalenko; Peter J. Steel; Victor I. Markov; Behrouz Forood

doi:10.1055/s-2001-13400

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Synthesis 2001(6): 0897-0903
DOI: 10.1055/s-2001-13400

PAPER

Synthesis of N,N-Disubstituted 3-Amino-1,2,4-triazoles

Alan R. Katritzky*^a, Boris V. Rogovoy^a,d, Vladimir Y. Vvedensky^a, Katherine Kovalenko^a,b, Peter J. Steel^c, Victor I. Markov^d, Behrouz Forood^e
^a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
^b A. E. Arbuzov Institute of Organic and Physical Chemistry, Arbuzov str. 8, Kazan 420088, Russia
^c Department of Chemistry, University of Canterbury, Christchurch 1, New Zealand
^d Ukrainian State Chemical Technology University (USChTU), Gagarina 8, Dniepropetrovsk, 49005, Ukraine
^e Exploratory Chemistry, Trega Biosciences, Inc., 9880 Campus Point Drive, San Diego, CA 92121, USA

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Publication History

Received 15 September 2000
Publication Date:
24 September 2004 (online)

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Abstract

A general method for the synthesis of N,N-disubstituted 3-amino-1,2,4-triazoles 5 from di(benzotriazolyl)methanimines 1 and 1 ′, hydrazine and substituted hydrazines is developed. The desired compounds were prepared regioselectively under mild conditions by simple procedures in yields of up to 95%.

Key words

acylation - cyclization - regioselectivity - triazoles - benzotriazole - hydrazines

References

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