Selective reaction of sulfanilamide with acetic anhydride catalyzed by stannous oxide nanoparticles

Document Type : Original Article

Authors

1 Department of Chemistry, Roudhen Branch, Islamic Azad University, Roudhen, Iran

2 Applied Chemistry Research Group, ACECR-Tehran Organization, Tehran, Iran

3 Researcher; PhD in Nanobiotechnology, University of Tehran, Tehran, Iran

Abstract

Sulfonamide compounds with functional group -SO2NH- show a wide range of biological activities and medicinal properties. The synthesis of sulfonamides has been of interest to medicinal chemists for a long time. In this article, the selective acylation of sulfanilamide with acetic anhydride was carried out using some catalysts with Lewis acid properties. In this research, the one-pot selective method of N-acylation of -SO2NH2 group in sulfanilamide molecule using stannous oxide nanoparticles as an efficient recyclable catalyst has been used. In this method, THF was replaced with expensive toxic amine solvents. The acylated product was identified by FTIR, 1HNMR, 13CNMR and MASS spectra. The best results with 85% efficiency, 95% selectivity were obtained using stannous oxide nanoparticles as catalyst (0.5 g) in tetrahydrofuran as solvent, at 60°C in 60 minutes. The catalyst was recycled three times and maintained its efficiency. Using this method is completely green and has economic and environmental benefits.

Keywords

Main Subjects

References

[1] Laudadio, G., et al., Sulfonamide synthesis through electrochemical oxidative coupling of amines and thiols. Journal of the American Chemical Society, 2019. 141(14): p. 5664-5668.
[2] Ghazviniyan, M., N. Masnabadi, and M.H. Ghasemi, Functionalized GO@ ZIF-90-supported sulfuric acid and its application in the catalytic synthesis of sulfonamides. Research on Chemical Intermediates, 2022: p. 1-14.
[3] Ghasemi, M.H., E. Kowsari, and S.K. Hosseini, Catalytic activity of magnetic Fe3O4@ Diatomite earth and acetic acid for the N-acylation of sulfonamides. Tetrahedron Letters, 2016. 57(3): p. 387-391.
[4] Massah, A., et al., P2O5/SiO2 as an efficient and recyclable catalyst for N-Acylation of sulfonamides under heterogeneous and solvent-free conditions. Journal of the Iranian Chemical Society, 2009. 6: p. 405-411.
[5] Thulam, V.K., et al., A novel and efficient method for N-acylation of sulfonamides and carbamates: their biological evaluation towards anti Malassezia activity. Journal of Pharmacy Research, 2013. 7(2): p. 195-199.
[6] Ong, J.-Y., et al., Isothiourea-catalyzed atroposelective N-acylation of sulfonamides. Organic Letters, 2020. 22(16): p. 6447-6451.
[7] Ghazviniyan, M., Masnabadi, N., & Ghasemi, M. H. (2023). A nanohybrid of Fe3O4/SnO magnetic recyclable catalyst for chemoselective N1-acylation of sulfanilamide under mild reaction conditions. Research on Chemical Intermediates, 1-16.
[8] Kang, H.H., et al., Metal oxide in aqueous organic solution promoted chemoselective N-sulfonylation of hydrophilic amino alcohols. Tetrahedron letters, 2003. 44(38): p. 7225-7227.
[9] Tamaddon, F., et al., ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters. Journal of Molecular Catalysis A: Chemical, 2011. 351: p. 41-45.
[10] Lv, J., et al., Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope. Green Chemistry, 2020. 22(20): p. 6936-6942.
[11] Ziegler, T., R. Dettmann, and J. Grabowski, Dibutyl tin oxide mediated, regioselective alkylation and acylation of siloxane protected glycopyranosides. Synthesis, 1999. 1999(09): p. 1661-1665.
[12] Kabir, A. and M.M. Matin, Regioselective acylation of a derivative of L-rhamonse using the dibutyltin oxide method. Journal of the Bangladesh Chemical Society, 1994. 7(1): p. 73-79.
[13] Bhande, S. S., Gaikwad, S. L., Pawar, B. G., Shaikh, A., Kolekar, S. S., Joo, O. S., Mane, R.S. & Han, S. H. (2013). Photoelectrochemical Studies of Chemically (Sol–Gel) Synthesized Tin Oxide Nanocrystallites. Journal of Nanoengineering and Nanomanufacturing, 3(3), 237-242.
[14] Boronat, M., Concepción, P., Corma, A., Renz, M., & Valencia, S. (2005). Determination of the catalytically active oxidation Lewis acid sites in Sn-beta zeolites, and their optimisation by the combination of theoretical and experimental studies. Journal of Catalysis, 234(1), 111-118
Applied Chemistry Today
Volume 19, Issue 71
June 2024
Pages 267-282

Files

Share

How to cite

Statistics