1,2,3-Triazoles as Leaving Groups in Purine Chemistry: a Three-Step Synthesis of N6-Substituted-2-Triazolyl-Adenine Nucleosides and Photophysical Properties thereof

Tetrahedron Letters 2013
Armands Kovaļovs, Irina Novosjolova, Ērika Bizdēna, Inga Bižāne, Lina Skardziute, Karolis Kazlauskas, Saulius Jursenas, Māris Turks

A novel three-step approach for the synthesis of N6-substituted-2-(1,2,3-triazol-1-yl)-adenine nucleosides is described. 2,6-Bis-(1,2,3-triazol-1-yl)purine nucleosides are obtained, which undergo regioselective nucleophilic aromatic substitution with amines at C(6). Thus, 1,2,3-triazoles are shown to be good leaving groups in purine chemistry. The title compounds exhibit interesting levels of fluorescence with quantum yields of up to 53%.

Keywords
Triazolyl purine derivatives; Nucleophilic aromatic substitution; Click chemistry; Fluorescence; Nucleoside analogs
DOI
10.1016/j.tetlet.2012.11.095
Hyperlink
http://www.sciencedirect.com/science/article/pii/S0040403912020497

Kovaļovs, A., Novosjolova, I., Bizdēna, Ē., Bižāne, I., Skardziute, L., Kazlauskas, K., Jursenas, S., Turks, M. 1,2,3-Triazoles as Leaving Groups in Purine Chemistry: a Three-Step Synthesis of N6-Substituted-2-Triazolyl-Adenine Nucleosides and Photophysical Properties thereof. Tetrahedron Letters, 2013, Vol.54, Iss.8, pp.850-853. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2012.11.095

Publication language
English (en)