Azolylpurines and azolylpurine nucleosides have important medicinal and biological applications. We have developed a novel approach for the synthesis of C(2) and C(6) modified purines and purine nucleoside analogues containing 1,2,3-triazolyl substituents. The method uses 2,6-diazidopurine derivatives as the key starting materials. The latter can be transformed into novel structural entities – 2,6-bis(1,2,3-triazol-1-yl)purine derivatives including ribo-, deoxyribo-, and arabino-nucleoside analogs. It was found that 1,2,3-triazolyl substituent acts as excellent leaving group. Additionally, regioselective SNAr reactions with various nucleophiles are possible at C(6). The range of nucleophiles include amines, thiols, amino acids and peptides, hydrazines, alcohols, and anilines. In the course of our research we have found that 2-(1,2,3-triazolyl)adenine/adenosine analogs (Nu = NY2) possess reasonable fluorescent properties that are conserved after the incorporation of nucleosides into short chain oligonucleotide.