title: Nucleoside azide-alkyne cycloaddition reactions under solvothermal conditions or using copper vials in a ball mill.
abstract: 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.
authors: a School of Chemistry and Chemical Engineering , Queen's University Belfast , Belfast , UK.
authors: Andrew J
authors: AJ
authors: Cummings
authors: Francesco
authors: F
authors: Ravalico
authors: Kegan I S
authors: KI
authors: McColgan-Bannon
authors: Olga
authors: O
authors: Eguaogie
authors: P Alain
authors: PA
authors: Elliott
authors: Matthew R
authors: MR
authors: Shannon
authors: Iris A
authors: IA
authors: Bermejo
authors: Angus
authors: A
authors: Dwyer
authors: Amanda B
authors: AB
authors: Maginty
authors: James
authors: J
authors: Mack
authors: Joseph S
authors: JS
authors: Vyle
mesh_terms: D000085:Acetates / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D008024:Ligands; D014230:Triazoles / Q000138:chemical synthesis*; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000085:Acetates; D000480:Alkynes; D001391:Azo Compounds; D008024:Ligands; D014230:Triazoles; D015215:Zidovudine; C007650:ethyl acetate; D003300:Copper
keywords: Synthetic methodology; green chemistry; modified nucleosides