Synlett 2016; 27(17): 2500-2504
DOI: 10.1055/s-0035-1562603
letter
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Free Preparation of 1,5-Disubstituted Triazoles by Alkylative Debenzylation of 1,4-Disubstituted Triazoles

Philip C. Bulman Page*
a   School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, Norfolk NR4 7TJ, UK   eMail: p.page@uea.ac.uk
,
G. Richard Stephenson*
a   School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, Norfolk NR4 7TJ, UK   eMail: p.page@uea.ac.uk
,
James Harvey
a   School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, Norfolk NR4 7TJ, UK   eMail: p.page@uea.ac.uk
,
Alexandra M. Z. Slawin
b   Molecular Structure Laboratory, School of Chemistry, University of St Andrews, Purdie Building, St. Andrews, Fife KY16 9ST, Scotland
› Institutsangaben
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Publikationsverlauf

Received: 15. Mai 2016

Accepted after revision: 29. Juni 2016

Publikationsdatum:
01. August 2016 (online)


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Abstract

A method that cleanly converts the 1,4-disubstituted 1,2,3-triazole products of the copper-catalyzed ‘click’ dipolar cycloaddition reaction of benzyl azide with terminal alkynes into 1,5-disubstituted triazoles is described. Selective N-alkylation of 1,4-disubstituted 1,2,3-triazoles under microwave irradiation is followed by debenzylation of the resulting 1,3,4-trisubstituted triazolium cations by treatment with potassium tert-butoxide.

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