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Synthesis 2006(12): 1943-1945  
DOI: 10.1055/s-2006-942381
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

5-Alkylamino-1H-1,2,3-triazoles by Base-Mediated Cleavage of Cycloadducts of Azides to Cyclic Ketene N,N-Acetals

Helmut Quast*, Manfred Ach, Thomas Hergenröther, Dieter Regnat
Institut für Organische Chemie der Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Fax: +49(541)8141935; e-Mail: hquast@uni-osnabrueck.de;
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Publication History

Received 12 December 2005
Publication Date:
08 May 2006 (online)

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Abstract

1,4,5-Trialkyltetrazolium salts are convenient synthetic equivalents for hypothetical secondary ynamines in cycloaddition reactions to azides. Thus, the tetrazolium salts are converted into alkylaminotriazoles via deprotonation, cycloaddition to azides, and subsequent base-mediated cleavage of the resulting spirocyclic cycloadducts.

Key words

amines - azides - cycloaddition - heterocycles - ring opening - spiro compounds

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