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Synthesis of Novel 1,2,3-triazolyl Benzoxazole Derivatives Using Deep Eutectic Solvents

The incidence and mortality caused by cancer is growing rapidly worldwide and it is necessary to find drugs for prevention and treatment. The benzoxazoe ring, as a privileged scaffold in medicinal chemistry, is widely incorporated in the structure of numerous bilogically active comounds and is found in drugs such as flunoxaprofen and zoxazolamine[1]. Benzoxazole derivatives have a wide range of biological activities such as antitumor, anti-HIV, antimicrobial, antinflammatory, antifungal and antiviral. Furthermore, 1, 2, 3-triazole plays an important role as a pharmacophore and exhibits remarkable biological activity.[2] In this work, new benzoxazole derivatives substituted with 1, 2, 3-triazole ring were prepared by click reaction using deep eutectic solvents (DES) which are known as preferred alternative solvents for organic synthesis due to their non-toxic, stable, non-flammable and inexpensive nature.[3] The key precursors of Schiff bases for the synthesis of target benzoxazole derivatives were prepared by the condensation reaction of the corresponding 4-hydroxybenzaldehyde and 2-aminophenol in the presence of ZnO nanoparticles as catalyst. By cyclization reaction of Schiff bases with NaCN, the corresponding 2-arylbenzoxazoles were prepared, which were then converted to O- propargylated benzoxazole derivatives by microwave reaction with propargyl bromide. The target 1, 2, 3-triazolyl benzoxazole derivatives were synthesized by Cu(I) catalyzed click reaction of the corresponding azides and O-propargylated benzoxazoles in DES (ChCl/glycerol and D- sorbitol/urea/ NH4Cl), and their structures were confirmed by NMR spectroscopy. [1] O. Derya, B. K. Celikates, B. Saglik, S. Levent, U. Cevik, Eur. J. Med. Chem. 2021, 15 [2] C. Chen, C. Holland, D. Depre, Eur. J. Org. Chem. 2019, 2020, 548-551 [3] Y. Riadi, O. Ouerghi, M. Gessi, H. Anouar, P. Guionneau, J. Mol. Liq. 2021, 323

benzoxazole ; 1, 2, 3-triazole ; click chemistry ; deep eutectic solventsectic solvents

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