Copper (I) Catalyzed Synthesis and Biological Evaluation of Tetrakis-1,2,3-Triazoles Based on D-Iditol

Author(s): Adnan Ibrahim Mohammed, Rasha Saad Jwad and Nabeela A. Al-Radha

This work describes the synthesis of D-iditol based tetrakis-1,2,3-triazoles. In the first approach, in which the heterocyclic portions were built from the click 1,3-dipolar cycloaddition of n-octyl azide, n-nonyl azide and n-decyl azide, respectively with propagyl alcohol. Alkynyl triazoles 4 a-c were readily prepared in very good yields under biphasic conditions from the corresponding triazolyl alcohols 3 a-c and propargyl bromide in the presence of NaOH pellets in DMF. 3,4-Diazido-3,4-dideoxy1,2 : 5,6-di-Oisopropylidene- D-iditol 7 was prepared in three subsequent steps from D-mannitol. The reaction of 7 with propargyl ethers 4 a-c under Cu (I)-catalyzed Huisgen-Meldal 1,3-dipolar cycloaddition conditions gave the desired tetrakis-1,2,3-triazole derivatives 8 a-c in very good yields. Removal of the acetal groups of 8 a-c using Amberlite IR 120 H+ in EtOH afforded the deprotected tetrakis triazoles 9 a-c in excellent yields. The synthesized compounds have characterized by TLC, FTIR, CHN and most of them by NMR. The biological activities of the synthesized compounds 8 and 9 were measured in vitro against different types of bacteria, some of the prepared compounds showed activity against the microorganism.

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