Tandem Oxidative alpha-Tosyloxylation of Alcohols/Nucleophilic Addition of Azide/Copper-Catalyzed 1,3-Dipolar Cycloaddition

An efficient method is described for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles (beta-keto-1,2,3-triazoles) in good to excellent yields by the successive treatment of secondary alcohols with [hydroxy(tosyloxy) iodo]benzene (Koser's reagent, HTIB), sodium azide followed by...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 24; pp. 4203 - 4207
Main Authors Reddy, P. Surendra, Sreedhar, B.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.12.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
beta-keto-1,2,3-triazoles
1,4-DISUBSTITUTED 1,2,3-TRIAZOLES
AZIDES
V-TRIAZOLES
ONE-POT SYNTHESIS
SOLID-PHASE
terminal alkynes
alpha-tosyloxylation
LIBRARIES
ALCOHOLS
MULTICOMPONENT REACTIONS
SOLUTION-PHASE
copper iodide
CHEMISTRY
secondary alcohols
1,3-dipolar cycloaddition
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Summary:An efficient method is described for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles (beta-keto-1,2,3-triazoles) in good to excellent yields by the successive treatment of secondary alcohols with [hydroxy(tosyloxy) iodo]benzene (Koser's reagent, HTIB), sodium azide followed by copper(I) iodide catalyzed 1,3-dipolar cycloaddition with terminal alkynes.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1217034