Modular synthesis of mono, di, and tri-1,4-disubstituted-1,2,3-triazoles through copper-mediated alkyne–azide cycloaddition

The synthesis of 1,2,3-triazoles was developed employing sequential copper azide–alkyne cycloaddition, tosylation, sodium azide, and copper azide–alkyne steps. This approach allowed the synthesis of two and three 1,2,3-triazole rings. A preliminary study to gain further insight into the reaction was...

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Bibliographic Details
Published in:Tetrahedron letters 2011-11, Vol.52 (46), p.6086-6090
Main Authors: Stefani, Hélio A., Canduzini, Hugo A., Manarin, Flávia
Format: Article
Language:English
Subjects:
1,2,3-Triazole
Alkynes
Chemistry
Click chemistry
Copper
Cycloaddition
Exact sciences and technology
Gain
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Modular
Organic chemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Preparations and properties
Propargyl alcohol
Sodium azides
Synthesis (chemistry)
Tetrahedrons
Ultrasonic chemistry
Ultrasound
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Summary:The synthesis of 1,2,3-triazoles was developed employing sequential copper azide–alkyne cycloaddition, tosylation, sodium azide, and copper azide–alkyne steps. This approach allowed the synthesis of two and three 1,2,3-triazole rings. A preliminary study to gain further insight into the reaction was performed using in situ ReactIR technology.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.09.004