Synthesis and Photophysical Studies on N1‐(Coumarin‐4′′′‐yl)‐C4‐(2′,3′‐dideoxyuridin‐3′‐yl/3′‐deoxythymidin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles

Abstract

AbstractA click chemistry‐based protocol has been utilized for the synthesis of a series of twelve novel tert‐butyldiphenylsilylated N1‐(coumarin‐4′′′‐yl)‐C4‐(2′,3′‐di‐deoxyuridin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles and N1‐(coumarin‐4′′′‐yl)‐C4‐(3′‐deoxythymin‐3′‐yl)‐oxymethyl‐1,2,3‐triazoles by utilising Cu(I)‐catalyzed azide‐alkyne cycloaddition reaction of 4‐azidocoumarins and 3′‐O‐(prop‐1‐yn‐3‐yl)‐5′‐O‐(tert‐butyldiphenylsilyl)‐2′,3′‐dideoxyuridin or 3′‐O‐(prop‐1‐yn‐3‐yl)‐5′‐O‐(tert‐butyldiphenylsilyl)‐3′‐deoxythymidin in 70–82 % and 68–82 % yields, respectively. The deprotection of resulted silylated uridine and thymidine conjugate with TBAF afforded title compounds in 81–91 % yield. The photophysical studies have been carried out on the synthesized coumarin‐triazolylmethyl nucleoside conjugates which revealed a very high Stokes shift value ranging from 82–215 nm.