Asymmetric synthesis of (1S,2S)-hydroxy cyclohexene-1,2,3-triazole derivatives

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Published: Dec 16, 2021
DOI: https://doi.org/10.14456/sehs.2021.34
Keywords:
click reaction triazole anti-tuberculosis

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Sufi An-Nur Abd Haris
Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Malaysia
Siti Sarah Shasuddin
Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Malaysia
Fazni Susila Abdul Ghani
Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Malaysia
Najmah P.S Hassan
Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Malaysia
Mohd Tajudin Mohd Ali
Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, Malaysia / Institute of Science, Universiti Teknologi MARA, Shah Alam, Malaysia. Corresponding author's e-mail: tajudinali@uitm.edu.my

Abstract

In this study, four (1S,2S)-hydroxycyclohexene-triazoles were synthezeid from 1,4-cyclohexadiene via epoxidation, epoxide ring-opening, and click reactions. The epoxidation of 1,4-cyclohexadiene yielded the monoepoxide cyclohexene. Subsequent epoxide ring-opening of epoxide catalyzed by the Salen
complex produced (1S,6S)-6-azidocyclohex-3-enol. These four (1S,2S)-hydroxycyclohexene-triazoles were synthesized via a final click reaction of (1S,6S)-6-azidocyclohex-3-enol with four different alkynes, i.e., propargyl amine, 2-propyn-1-ol, propargyl bromide, and 1-ethylanisole.

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How to Cite
Haris, S. A.-N. A., Shasuddin, S. S., Susila Abdul Ghani, F., Hassan, N. P., & Mohd Ali, M. T. (2021). Asymmetric synthesis of (1S,2S)-hydroxy cyclohexene-1,2,3-triazole derivatives. Science, Engineering and Health Studies, 15, 21020007. https://doi.org/10.14456/sehs.2021.34
Issue
Volume 15, 2021
Section
Physical sciences
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This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

References

Ali, M. T. M., Zahari, H., Aliasak, A., Lim, S. M., Ramasamy, K., and Macabeo, A. P. G. (2017a). Synthesis, characterization and cytotoxic activity of betulinic acid and Seco-betulinic acid derivatives against human colorectal carcinoma. Oriental Journal of Chemistry, 33(1), 242-248.

Ali, M. T. M., Aliasak, S. A., and Macabeo, A. P. G. (2017b). Short asymmetric synthesis of a model monomeric unit for α/γ peptide foldamers based on β-amino linked D-leucine-cis-γ-butyrolactone γ-acetic acid conjugate. Organic Communications, 10(2), 99-103.

Ali, M. T. M., Husin, M. Z., and Macabeo, A. P. G. (2021). Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone. ACS Omega, 6(38), 24614-24618.

Ali, M. T. M., Macabeo, A. P. G., Wan, B., Franzblau, S., and Reiser, O. (2013). Asymmetric approach toward new conformationally constrained cis-gamma butyrolactone. In Proceedings of the American Chemical Society, pp. 245. New Orleans, USA.

Chiong, M. R., and Paraan, F. N. C. (2019). Controlling the nucleophilic properties of cobalt salen complexes for carbon dioxide capture. RSC Advances, 40(9), 23254-23260.

Hein, J. E., and Fokin, V. V. (2010). Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides. Chemical Society Reviews, 39(4), 1302-1315.

Kim, W. G., Baek, S. Y., Jeong, S. Y., Nam, D., Jeon, J. H, Choe, W., Baik, M. H., and Hong, S. Y. (2020). Chemo- and regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition. Organic and Biomolecular Chemistry, 18(17), 3374-3381.

Martinez, L. E., Leighton, J. L., Carsten, D. H., and Jacobsen, E. N. (1995). Highly enantioselective ring opening of epoxides catalyzed by (salen)Cr(III) Complexes. Journal of the American Chemical Society, 117(21), 5897-5898.

Matin, A., Gavande, N., Kim, M. S., Yang, N. X., Salam, N. K., Hanrahan, J. R., Roubin, R. H., and Hibbs, D. E. (2009). 7-Hydroxy-benzopyran-4-one derivatives: a novel pharmacophore of peroxisome proliferator-activated receptor alpha and gamma (PPAR α and γ) dual agonists. Journal of Medicinal Chemistry, 52(21), 6835-6850.

Kharb, R., Sharma, P. C., and Yar, M. S. (2011). Pharmacological significance of triazole scaffold. Journal of Enzyme Inhibition and Medicinal Chemistry, 26(1), 1-21.

Thirumurugan, P., Matosiuk, D., and Jozwiak, K. (2013). Click chemistry for drug development and diverse chemical-biology applications. Chemical Review, 113(7), 4905-4979.

Totobenazara, J., and Burke, A. J. (2015). New click-chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications. Tetrahedron Letters, 56(22), 2853-2859.

Zhang, X., He‚ Y., Liu‚ S., Yu‚ Z., Jiang‚ Z., Yang, Z., Dong‚ Y., Nabinger, S. C., Wu‚ L., Gunawan‚ A. M., Wang‚ L., Chan, R. J., and Zhang, Z. (2010). Salicylic acid based small molecule inhibitor for the oncogenic Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2). Journal of Medicinal Chemistry, 53(6), 2482-2493.

Zhang, H., Ryono, D. E., Devasthale, P., Wang, W., O’Malley, K., Farrelly, D., Gu, L., Harrity, T., Cap, M., Chu, C., Locke, K., Zhang, L., Lippy, J., Kunselman, L., Morgan, N., Flynn, N., Moore, L., Hosagrahara, V., Zhang, L., . . . Cheng, P. T. W. (2009). Design, synthesis and structure-activity relationships of azole acids as novel, potent dual PPAR α/γ agonists. Bioorganic and Medicinal Chemistry Letters, 19(5), 1451-1456.