Allyl-Assisted, Cu(I)-Catalyzed Azide–Alkyne Cycloaddition/Allylation Reaction: Assembly of the [1,2,3]Triazolo-4,5,6,7-tetrahydropyridine Core Structure
We report a Cu(I)-catalyzed azide–alkyne–allyl halide three-component reaction for a one-pot synthesis of 1,4-disubstituted 5-allyl-1,2,3-triazoles. The allyl moiety provides not only the electrophile but also a coordinating ligand to Cu, which is essential for the reaction to occur under mild cond...
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Published in | Journal of organic chemistry Vol. 80; no. 21; pp. 11003 - 11012 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
06.11.2015
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | We report a Cu(I)-catalyzed azide–alkyne–allyl halide three-component reaction for a one-pot synthesis of 1,4-disubstituted 5-allyl-1,2,3-triazoles. The allyl moiety provides not only the electrophile but also a coordinating ligand to Cu, which is essential for the reaction to occur under mild conditions. A concise synthesis of a potential drug candidate 1 is realized based on this key reaction. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.5b02174 |