title: Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization.
abstract: Treatment of toyocamycin or sangivamycin with 1,3-dibromo-5,5-dimethylhydantoin in MeOH (r.t./30 min) gave 8-bromotoyocamycin and 8-bromosangivamycin in good yields. Nucleophilic aromatic substitution of 8-bromotoyocamycin with sodium azide provided novel 8-azidotoyocamycin. Strain promoted click reactions of the latter with cyclooctynes resulted in the formation of the 1,2,3-triazole products. Iodine-mediated direct C8-H bond functionalization of tubercidin with benzotriazoles in the presence oftert-butyl hydroperoxide gave the corresponding 8-benzotriazolyltubercidin derivatives. The 8-(1,2,3-triazol-1-yl)-7-deazapurine derivatives showed moderate quantum yields and a large Stokes shifts of ~ 100 nm.
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Sam
authors.initials: S
authors.lastname: Kavoosi
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Ramanjaneyulu
authors.initials: R
authors.lastname: Rayala
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Brenna
authors.initials: B
authors.lastname: Walsh
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Maria
authors.initials: M
authors.lastname: Barrios
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Walter G
authors.initials: WG
authors.lastname: Gonzalez
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Jaroslava
authors.initials: J
authors.lastname: Miksovska
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Logesh
authors.initials: L
authors.lastname: Mathivathanan
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Raphael G
authors.initials: RG
authors.lastname: Raptis
authors.affiliation: Florida International University, Department of Chemistry and Biochemistry, Miami, Florida, 33199, United States.
authors.forename: Stanislaw F
authors.initials: SF
authors.lastname: Wnuk
keywords: Azido Nucleosides; Click Chemistry; Deazapurine nucleosides; Direct C-H Functionalization; Fluorescence; Triazoles