Effective Use of Oxalyl Chloride Compound in Synthesis of Oxalohydrazide and Parabanic Acid Derivatives

Year 2023, Volume: 1 Issue: 2, 81 - 86, 30.11.2023

İbrahim Evren Kıbrız , Mustafa Saçmacı , İsmail Yıldırım

Abstract

Oxalyl chloride, (COCl)2, as an easily available chemical, is one of the organic reagents that are highly applicable in chemical reactions. It is used as the starting material of various chemical transformations such as ring closure in organic reactions, ring opening of epoxides, chlorination, and formylation. In this context, we report the reactions of oxalyl chloride (1) with cyanoacetyl hydrazide (2) and N,N'-diarylcarbazone (3) for the first time here. Compounds (4 and 5) characterized by elemental analysis, 1H, and 13C-NMR spectra are conformable by structure.

Keywords

Oxalyl Chloride, Carbazone, Cyanoacetyl hydrazide, Oxalohydrazid, Parabanic Acid

References

• R. Salmon and I. V. Efremov, “in Encyclopedia of Reagents for Organic Synthesis,” John Wiley & Sons, Weinheim, 2001.
• A. Fauconnier, “The Action of Phosphorus Pentachloride on Diethyl Oxalate,” Comptes Rendus Acad. Sci., vol. 114, pp. 122–123, 1892.
• W. Li, Y. Asada, and T. Yoshikawa, “Antimicrobial Flavonoids from Glycyrrhiza Glabra Hairy Root Cultures,” Planta Med., vol. 64, pp. 746–747, Dec. 1998, doi:10.1055/s-2006-957571.
• S. Jang, S. Jeung, K. Kim, H. Kim, H. Yu, R. Park, H. Kim, and Y. You, “Tanshinone IIA from Salvia miltiorrhiza Inhibits Inducible Nitric Oxide Synthase Expression and Production of TNF-α, IL-1β and IL-6 in Activated RAW 264.7 Cells,” Planta Med., vol. 69, pp. 1057–1059, Nov. 2003, doi:10.1055/s-2003-45157.
• G. B. M. Bettòlo, C. G. Casinovi, and C. Galeffi, “A New Class of Quinones: Sesquiterpenoid Quinones of Mansonia altissima Chev,” Tetrahedron Lett., vol. 52, pp. 4857–4864, 1965, doi: 10.1016/S0040-4039(01)89048-1.
• C. C. Shen, “Phenolic Constituents of the Roots of Sophora flavescens,” J. Nat. Prod., vol. 69, pp. 1237–1240, Aug. 2006, doi:10.1021/np060189d.
• M. Knaack, P. Emig, J. W. Bats, M. Kiesel, A. Müller, and E. Günther, “Synthesis and Characterization of the Biologically Active 2-[1-(4-chlorobenzyl)-1H-indol-3-yl] -2-oxo-N-pyridin-4-yl acetamide,” Eur. J. Org. Chem., vol. 2001, pp. 3843–3847, Sep. 2001, doi:10.1002/1099-0690(200110)2001:20<3843::AID-EJOC3843>3.0.CO;2-P.
• M. D. Armistead, W. M. Harding, J. O. Saunders, and S. J. Boger, “Biologically Active Acylated Amino Acid Derivatives,” United States Patent. US 5723459, 1998.
• B. R. Bacon, S. C. Gordon, E. Lawitz, P. Marcellin, J. M. Vierling, S. Zeuzem. F. Poordad, Z. D. Goodman, H. L. Sings, N. Boparai, M. Burroughs, C. A. Brass, J. K. Albrecht, and R. Esteban, “Boceprevir for Previously Treated Chronic HCV Genotype 1 Infection,” N. Engl. J. Med., vol. 364, pp. 1207–1217, Mar. 2011, doi:10.1056/NEJMoa1009482.
• T. F. Hartley, P. L. Lieberman, E. O. Meltzer, J. N. Noyes, D. S. Pearlman, and D. G. Tinkelman, “Efficacy and Tolerance of Fluocortin Butyl Administered Twice Daily in Adult Patients with Perennial Rhinitis,” J. Allergy Clin. Immunol., vol. 75, pp. 501–507, Apr. 1985, doi:10.1016/s0091-6749(85)80024-5.