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. 2021 Apr 12;26(8):2224.
doi: 10.3390/molecules26082224.

Synthesis of 4-Arylselanyl-1 H-1,2,3-triazoles from Selenium-Containing Carbinols

Francesca Begini  1 , Renata A Balaguez  2 , Allya Larroza  2 , Eric F Lopes  2 , Eder João Lenardão  2 , Claudio Santi  1 , Diego Alves  2
Affiliations

Synthesis of 4-Arylselanyl-1 H-1,2,3-triazoles from Selenium-Containing Carbinols

Francesca Begini et al. Molecules. .

Abstract

In this work, we present a simple way to achieve 4-arylselanyl-1H-1,2,3-triazoles from selenium-containing carbinols in a one-pot strategy. The selenium-containing carbinols were used as starting materials to produce a range of selanyl-triazoles in moderate to good yields, including a quinoline and Zidovudine derivatives. One-pot protocols are crucial to the current concerns about waste production and solvent consumption, avoiding the isolation and purification steps of the reactive terminal selanylalkynes. We could also isolate an interesting and unprecedented by-product with one alkynylselenium moiety connected to the triazole.

Keywords: 1,2,3-triazoles; carbinols; click chemistry; cycloaddition; heterocycles; selenium.

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Conflict of interest statement

The authors declare no conflict of interests.

Figures

Figure 1
Figure 1
Previous protocols to prepare 5-arylselanyl- and 4-arylselanyl-1H-1,2,3-triazoles.
Scheme 1
Scheme 1
Synthesis of 4-arylselanyl-1H-1,2,3-triazoles from selenium-containing carbinols.
Scheme 2
Scheme 2
4-Arylselanyl-1H-1,2,3-triazoles 4a-f: scope of arylselanyl carbinols 1.
Scheme 3
Scheme 3
4-Arylselanyl-1H-1,2,3-triazoles 4g-n: scope of azides 3.
Scheme 4
Scheme 4
By-products 5a and 5b from the reaction of 3a or 3c with 2a generated in situ.
See this image and copyright information in PMC

References

    1. Dehaen W., Bakulev V.A., editors. Chemistry of 1,2,3-Triazoles. Volume 40. Springer International Publishing; Cham, Switzerland: 2015. Topics in Heterocyclic Chemistry.
    1. Themed collection: Click chemistry: Function follows form. Chem. Soc. Rev. 2010;39:1221–1407. - PubMed
    1. Bertozzi C.R. A Decade of Bioorthogonal Chemistry, Themed collection: Bioorthogonal Chemistry in Biology. Acc. Chem. Res. 2011;44:651–840. doi: 10.1021/ar200193f. - DOI - PMC - PubMed
    1. Costa G.P., Baldinotti R.S.M., Fronza M.G., Nascimento J.E.R., Dias I.F.C., Sonego M.S., Seixas F.K., Collares T., Perin G., Jacob R.G., et al. Synthesis, Molecular Docking, and Preliminary Evaluation of 2-(1,2,3-Triazoyl)benzaldehydes as Multifunctional Agents for the Treatment of Alzheimer’s Disease. ChemMedChem. 2020;15:610–622. doi: 10.1002/cmdc.201900622. - DOI - PubMed
    1. Begnini K.R., Duarte W.R., da Silva L.P., Buss J.H., Goldani B.S., Fronza M., Segatto N.V., Alves D., Savegnago L., Seixas F.K., et al. Apoptosis Induction by 7-Chloroquinoline-1,2,3-Triazoyl Carboxamides in Triple Negative Breast Cancer Cells. Biomed. Pharmacother. 2017;91:510–516. doi: 10.1016/j.biopha.2017.04.098. - DOI - PubMed

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