Synthesis and characterization of new 1,4 and 1,5-disubstituted glucopyranosyl 1,2,3-triazole by 1,3-dipolar cycloaddition

A series of 1,4 and 1,5-disubstituted 1-(β- d-glucopyranosyl)-1,2,3-triazoles has been prepared in an efficient manner with excellent yields using the intermolecular 1,3-dipolar cycloaddition of 1-azido-2,3,4,6-tetra- O-acetyl-β- d-glucopyranose 2 to a variety of substituted alkynes phenylacethylene...

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Bibliographic Details
Published in:Journal of molecular structure 2009-07, Vol.929 (1), p.6-9
Main Authors: El Moncef, Abdelkarim, El Hadrami, El Mestafa, Ben-Tama, Abdeslem, de Arellano, Carmen Ramírez, Zaballos-Garcia, Elena, Stiriba, Salah-Eddine
Format: Article
Language:English
Subjects:
1,2,3-Triazole
1,3-Dipolar cycloaddition
Crystal structure
Dipolarophile
Glucopyranosyl azide
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Summary:A series of 1,4 and 1,5-disubstituted 1-(β- d-glucopyranosyl)-1,2,3-triazoles has been prepared in an efficient manner with excellent yields using the intermolecular 1,3-dipolar cycloaddition of 1-azido-2,3,4,6-tetra- O-acetyl-β- d-glucopyranose 2 to a variety of substituted alkynes phenylacethylene 3, propargyl alcohol 4, 2-butyn-1,4-diol, 5, 3-propargylbenzimidazole 6 and propargylpyrazole 7 in toluene. The reaction takes place with the formation of both 4- and 5-regioisomers.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2009.03.036