Synthesis, Characterization and Theoretical Study of 2,4-diaryl-1,3-Selenazole

doi:https://doi.org/10.5281/zenodo.15772101

Biomedicine and Chemical Sciences

2024, Volume 3, Issue 1 : 10-18 doi: https://doi.org/10.5281/zenodo.15772101

Research Article

Synthesis, Characterization and Theoretical Study of 2,4-diaryl-1,3-Selenazole

Anwar Talib Abdulwahid

Ali Jameel Hameed

DOI : https://doi.org/10.5281/zenodo.15772101

Received

Oct. 20, 2023

Revised

Dec. 8, 2023

Accepted

Dec. 10, 2023

Published

Jan. 1, 2024

Abstract

The synthesis of two new 2,4-diaryl-1,3-selenazoles series were achieved by subjecting primary arylselenocarboxylic amides to cyclization with α-bromoketones. The systematic preparation of 2,4-diaryl-1,3-selenazoles was carried out by the primary selenoamides with α-halo ketones. Selenoamides were obtained from the reaction of NaHSe with aryl nitrile .The resulting 2,4-diary-1,3-selenazoles have been characterized by different spectroscopic methods; such as ¹H ,¹³C NMR, IR, and mass spectroscopic data to prove the structural formula of the prepared compounds. Theoretical study has been carried out by using DFT theory to study the structural and electronic properties of prepared compounds.

Keywords

4-diaryl-1

3-selenazoles

NaHSe

Organoselenium compounds

Α-bromoketones

REFERENCES

Abdullah, S. A., Ali, D. S., & Hameed, A. J. (2020). A study of the biological activity of 4-(Para-Substituted phenyl)-1, 2, 3-Selenadiazole derivatives as anti-oxidant and anti-breast cancer. Basrah Journal of Science, 38(3), 480-496.
Alias, N. Z., Idris, M. H. M., Somat, N. A., Mahmud, N., Hasan, S., Lam, K. W., ... & Hassan, N. I. (2020). Synthesis, antioxidant, anticholinesterase activities and molecular docking studies of coumaryl 1, 3-selenazoles derivatives. Preprints.
Al-Rubaie, A. Z., Al-Masoudi, W. A., Hameed, A. J., Yousif, L. Z., & Graia, M. (2008). Synthesis, reaction and antiviral activity of 2, 4-diaryl-1, 3-selenazoles. Journal of the Korean Chemical Society, 52(1), 36-46.
Al-Rubaie, A. Z., Yousif, L. Z., & Al-Hamad, A. J. (2002). Palladium-catalyzed formation of 3, 5-diaryl-1, 2, 4-selenadiazoles from arylselenocarboxamide. Journal of Organometallic Chemistry, 656(1-2), 274-280. https://doi.org/10.1016/S0022-328X(02)01631-5
Alsawad, D. H., Al-Riyahee, A. A., & Hameed, A. J. (2021, November). Simulation Study of Structural and Electronic Properties for Adducts complexes of Bis (Acetylacetonato) oxoVandium (IV) with 4-(Para-substituted phenyl)-1, 2, 3-Selenadiazole. In Journal of Physics: Conference Series (Vol. 2063, No. 1, p. 012002). IOP Publishing. https://doi.org/10.1088/1742-6596/2063/1/012002
Atkins, P. (2010). Shriver and Atkins' inorganic chemistry. Oxford University Press, USA.
Beswick, M. A., Harmer, C. N., Raithby, P. R., Steiner, A., Tombul, M., & Wright, D. S. (1999). Reactions of organolithium complexes with elemental selenium: insertion producing [PhC CSeLi· TMEDA· THF] 1 and cyclisation producing [{PhC} 4Se] 2 (TMEDA=[Me2NCH2] 2). Journal of organometallic chemistry, 573(1-2), 267-271. https://doi.org/10.1016/S0022-328X(98)00830-4
Cordes, D. B., Hua, G., Slawin, A. M., & Woollins, J. D. (2011). 2, 5-Diaryl-1, 3, 4-selenadiazoles prepared from Woollins' reagent. Crystal Structure Communications, 67(12), o509-o514. https://doi.org/10.1107/S0108270111049900
Dzedulionytė, K., Voznikaitė, P., Bieliauskas, A., Malinauskienė, V., Sløk, F. A., & Šačkus, A. (2021). Methyl 2-amino-4-[1-(tert-butoxycarbonyl) azetidin-3-yl]-1, 3-selenazole-5-carboxylate. Molbank, 2021(2), M1207. https://doi.org/10.3390/M1207
Etesam, L., Mosslemin, M. H., & Hassanabadi, A. (2022). A simple, one-pot method for the synthesis of functionalized selenazole derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 197(12), 1273-1276. https://doi.org/10.1080/10426507.2022.2096609
Geisler, K., Jacobs, A., Künzler, A., Mathes, M., Girrleit, I., Zimmermann, B., ... & Langer, P. (2002). Efficient synthesis of primary selenocarboxylic amides by reaction of nitriles with phosphorous (V) selenide. Synlett, 2002(12), 1983-1986. https://doi.org/10.1055/s-2002-35604
Hansch, C., & Leo, A. (1995). Exploring quantitative structure-activity relationships (QSAR); Fundamentals and applications in chemistry and biology. American Chemical Society.
Hua, G., Cordes, D. B., Du, J., Slawin, A. M., & Woollins, J. D. (2018). Diverse derivatives of selenoureas: A synthetic and single crystal structural study. Molecules, 23(9), 2143. https://doi.org/10.3390/molecules23092143
Hua, G., Du, J., Slawin, A. M., & Woollins, J. D. (2014). A synthetic and structural study of arylselenoamides and 2, 4-diaryl-1, 3-selenazoles. Synlett, 25(15), 2189-2195. https://doi.org/10.1055/s-0034-1378525
Hua, G., Henry, J. B., Li, Y., Mount, A. R., Slawin, A. M., & Woollins, J. D. (2010). Synthesis of novel 2, 5-diarylselenophenes from selenation of 1, 4-diarylbutane-1, 4-diones or methanol/arylacetylenes. Organic & Biomolecular Chemistry, 8(7), 1655-1660. https://doi.org/10.1039/B924986A
Hua, G., Li, Y., Fuller, A., Slawin, A. M. Z., & Woollins, J. D. (2009). Facile synthesis and structure of novel 2, 5-disubstituted 1, 3, 4-selenadiazoles. European Journal of Organic Chemistry, 2009(10), 1612-1618. https://doi.org/10.1002/ejoc.200900013
Jalbout, A. F., Hameed, A. J., & Essa, A. H. (2008). Structural isomers of 2-(2, 3 and 4-substituted-phenyl)-1, 2-benzisoselenazol-3 (2H)-one: A Theoretical Study. Journal of Organometallic Chemistry, 693(12), 2074-2078. https://doi.org/10.1016/j.jorganchem.2008.02.026
Jalbout, A. F., Hameed, A. J., Jimenez-Fabian, I., Ibrahim, M., & De Leon, A. (2008). Chalcanthrene–fullerene complexes: A theoretical study. Journal of Organometallic Chemistry, 693(2), 216-220. https://doi.org/10.1016/j.jorganchem.2007.09.036
Koketsu, M., & Ishihara, H. (2003). Synthesis of 1, 3-selenazine and 1, 3-selenazole and their biological activities. Current Organic Chemistry, 7(2), 175-185. https://doi.org/10.2174/1385272033373102
Li, Y., Hua, G. X., Slawin, A. M., & Woollins, J. D. (2009). The X-ray crystal structures of primary aryl substituted selenoamides. Molecules, 14(2), 884-892. https://doi.org/10.3390/molecules14020884
Ranu, B. C., & Banerjee, B. (Eds.). (2020). Organoselenium Chemistry. Walter de Gruyter GmbH & Co KG.
Sonawane, A. D., & Koketsu, M. (2022). 1, 3-Selenazoles. Comprehensive Heterocyclic Chemistry IV. https://doi.org/10.1016/B978-0-12-818655-8.00089-5
Tanini, D., & Capperucci, A. (2020). Recent advances in the synthesis of five-and six-membered selena-heterocycles. Target in heterocyclic systems: chemistry and properties, 2020, 289-319.
Tao, S., Xu, L., Yang, K., Zhang, J., & Du, Y. (2022). Construction of the 2-amino-1, 3-selenazole skeleton via PhICl2/KSeCN-mediated selenocyanation/cyclization. Organic Letters, 24(23), 4187-4191. https://doi.org/10.1021/acs.orglett.2c01468
Wirth, T. (2003). Introduction and general aspects. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, 1-4. https://doi.org/10.1007/3-540-46114-0_1

Recommended Articles

Original Article Open Access

A FRAMEWORK OF MONOCLONAL ANTIBODIES AND RELATED PRODUCTION ENGINEERING

Navneet Kumar Verma

2025, Volume 4, Issue 4 : 26-34

Download PDF

Research Article Open Access

Investigation of Tritrichomonas Foetus in Cattle Using Different Methods in Basrah City – Iraq

Muntaha A. H. Nasir ,

Al-Idreesi S.R. ,

Wasfi A. Al-Masoudi

2023, Volume 2, Issue 1 : 39-43

DOI: https://doi.org/10.48112/bcs.v2i1.334

Download PDF

Research Article Open Access

The Role of Vitamin D and Zinc In Facing COVID-19 Injury

Yazi Abdullah Jassima

2022, Volume 1, Issue 1 : 6-10

DOI: https://doi.org/10.48112/bcs.v1i1.76

Download PDF

Research Article Open Access

Design and Synthesis Ligands Tetradents Substituted with Halogenes in α- Position and Conjugation with Riboflavin (Bioconjugates)

Nasser Thallaj

2022, Volume 1, Issue 2 : 47-56

DOI: https://doi.org/10.48112/bcs.v1i2.85

Download PDF

Biomedicine and Chemical Sciences journal thumbnail

Volume 3, Issue 1

Downloads

Download PDF xml

Download XML

Citations

2 Views

0 Downloads

Share this article

License

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

All papers should be submitted electronically. All submitted manuscripts must be original work that is not under submission at another journal or under consideration for publication in another form, such as a monograph or chapter of a book. Authors of submitted papers are obligated not to submit their paper for publication elsewhere until an editorial decision is rendered on their submission. Further, authors of accepted papers are prohibited from publishing the results in other publications that appear before the paper is published in the Journal unless they receive approval for doing so from the Editor-In-Chief.

Biomed. Chem. Sci. open access articles are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License. This license lets the audience to give appropriate credit, provide a link to the license, and indicate if changes were made and if they remix, transform, or build upon the material, they must distribute contributions under the same license as the original.