Abstract
We have developed an efficient, CuI-catalyzed, microwave-assisted method for the synthesis of bis-1,2,3-triazole derivatives starting from a 3,4,6-tri-\(O\)-acetyl-d-glucal-derived mesylate. This mesylate was obtained from 3,4,6-tri-\(O\)-acetyl-d-glucal through \(C\)-glycosidation, deprotection of acetate groups to alcohols, and selective mesylation of the primary alcohol. This mesylate moiety was then converted to an azide through a microwave-assisted method with good yield. The azide, once synthesized, was then treated with different terminal alkynes in the presence of CuI to synthesize various bis-triazoles in high yields and short reaction times.
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Acknowledgments
The authors gratefully acknowledge financial support from the São Paulo Research Foundation (FAPESP, Grant 2012/00424-2 and fellowship to FBS 2013/20553-4) and National Council for Scientific and Technological Development (CNPq) for a fellowship (308.320/2010–7 to HAS).
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Shamim, A., Souza, F.B., Trossini, G.H.G. et al. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-\(\varvec{O}\)-acetyl-D-glucal. Mol Divers 19, 423–434 (2015). https://doi.org/10.1007/s11030-014-9564-0
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DOI: https://doi.org/10.1007/s11030-014-9564-0