Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill

Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5′-azido-5′-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5 mol% Cu(I) in the...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2015, Vol.34 (5), p.361-370
Main Authors: Cummings, Andrew J., Ravalico, Francesco, McColgan-Bannon, Kegan I. S., Eguaogie, Olga, Elliott, P. Alain, Shannon, Matthew R., Bermejo, Iris A., Dwyer, Angus, Maginty, Amanda B., Mack, James, Vyle, Joseph S.
Format: Article
Language:English
Subjects:
Acetates - chemistry
Alkynes - chemistry
Azo Compounds - chemistry
Catalysis
Click Chemistry
Copper - chemistry
Cycloaddition Reaction
green chemistry
Ligands
modified nucleosides
Synthetic methodology
Triazoles - chemical synthesis
Zidovudine - analogs & derivatives
Zidovudine - chemistry
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Summary:Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5′-azido-5′-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5 mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32 ″ (2.38 mm) diameter copper ball (62 mg) at 60 Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5′-azido nucleoside with clean conversion to the corresponding 1,3-triazole.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770.2014.1001855