Efficient Atropodiastereoselective Access to 5,5′-Bis-1,2,3-triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors
Publication type: Journal Article
Publication date: 2014-03-27
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
24677199
General Chemistry
Catalysis
Organic Chemistry
Abstract
Halide decides: The use excess CuI-halide (X=Br, I) in azide–alkyne cycloadditions leads to predominant formation of 5-halogeno-1,2,3-triazoles (see scheme). In contrast, with CuCl, the major products exhibit two 5,5′-linked triazole rings and represent an efficient and highly atropodiastereoselective access to glucose-based 5,5′-bis-triazoles. Subsequent Pd-catalyzed Sonogashira and Suzuki couplings afforded 5-alkynylated and 5-phenyl derivatives in good yield. The products moderately inhibit glycogen phosphorylase.
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37
Total citations:
37
Citations from 2025:
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(13.51%)
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Goyard D. et al. Efficient Atropodiastereoselective Access to 5,5′-Bis-1,2,3-triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors // Chemistry - A European Journal. 2014. Vol. 20. No. 18. pp. 5423-5432.
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Chajistamatiou A. S., Sotiropoulou A. I., Chrysina E. D. Efficient Atropodiastereoselective Access to 5,5′-Bis-1,2,3-triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors // Chemistry - A European Journal. 2014. Vol. 20. No. 18. pp. 5423-5432.
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TY - JOUR
DO - 10.1002/chem.201304989
UR - https://doi.org/10.1002/chem.201304989
TI - Efficient Atropodiastereoselective Access to 5,5′-Bis-1,2,3-triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors
T2 - Chemistry - A European Journal
AU - Chajistamatiou, Aikaterini S
AU - Sotiropoulou, Anastasia I
AU - Chrysina, Evangelia D.
PY - 2014
DA - 2014/03/27
PB - Wiley
SP - 5423-5432
IS - 18
VL - 20
PMID - 24677199
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2014_Goyard,
author = {Aikaterini S Chajistamatiou and Anastasia I Sotiropoulou and Evangelia D. Chrysina},
title = {Efficient Atropodiastereoselective Access to 5,5′-Bis-1,2,3-triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors},
journal = {Chemistry - A European Journal},
year = {2014},
volume = {20},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/chem.201304989},
number = {18},
pages = {5423--5432},
doi = {10.1002/chem.201304989}
}
Cite this
MLA
Copy
Goyard, David, et al. “Efficient Atropodiastereoselective Access to 5,5′-Bis-1,2,3-triazoles: Studies on 1-Glucosylated 5-Halogeno 1,2,3-Triazoles and Their 5-Substituted Derivatives as Glycogen Phosphorylase Inhibitors.” Chemistry - A European Journal, vol. 20, no. 18, Mar. 2014, pp. 5423-5432. https://doi.org/10.1002/chem.201304989.