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

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• 作者：Armands Kova?ovs^a ; Irina Novosjolova^a ; ¨¥rika Bizd¨¥na^a ; Inga Bi?¨¡ne^a ; Lina Skardziute^b ; Karolis Kazlauskas^b ; Saulius Jursenas^b ; M¨¡ris Turks^a ; ^{maris_turks@ktf.rtu.lv}
• 关键词：Triazolyl purine derivatives ; Nucleophilic aromatic substitution ; Click chemistry ; Fluorescence ; Nucleoside analogs
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：20 February, 2013
• 年：2013
• 卷：54
• 期：8
• 页码：850-853
• 全文大小：1134 K

文摘

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 % .