CuBr-NCS-Mediated Multicomponent Azide-Alkyne Cycloaddition: Mild and Efficient Synthesis of 5-Bromo-1,4-Disubstituted-1,2,3-Triazoles

Abstract CuBr-NCS was found to be a mild and efficient reaction system to promote the multicomponent azide-alkyne cycloaddition reactions. Under the reaction conditions, terminal alkynes and azides can react smoothly at ambient temperature to give the target products 5-bromo-1,4-disubsituted-1,2,3-t...

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Bibliographic Details
Published in:Synlett 2011-04, Vol.2011 (6), p.874-878
Main Authors: Li, Lingjun, Li, Ran, Zhu, Anlian, Zhang, Guisheng, Zhang, Lihe
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
letter
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
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Summary:Abstract CuBr-NCS was found to be a mild and efficient reaction system to promote the multicomponent azide-alkyne cycloaddition reactions. Under the reaction conditions, terminal alkynes and azides can react smoothly at ambient temperature to give the target products 5-bromo-1,4-disubsituted-1,2,3-triazoles in moderate to good yields with a wide tolerance of other sensitive functional groups. The further successful application of the CuBr-NCS reaction system in sugar and cyclic adenosine 5′-diphosphoribose (cADPR) analogues illustrated the value of this method in the synthesis of designed biomolecules.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259908