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Reactivity of N'-substituted N-(4-pentynoyl)thioureas and N-[2-(2-propynyl)-4-pentynoyl]thioureas

P. Kutschy, P. Kristian, M. Dzurilla, D. Koščík, and R. Nádaskay

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, P. J. Šafárik University, CS-04167 Košice


Abstract: Treatment of jV-(4-pentynoyl)- and jV-[2-(2-propynyl)-4-pentynoyl]thioureas with sodium ethoxide and mercury(II) chloride or acetate, respectively, results in splitting-offof acyl residue under formation of N-sub­stituted thioureas. On heating 4-{7V-[2-(2-propynyl)-4-pentynoyl]thiocarbamoyl} morpholine in ethanol under catalytic action of titanium(IH) chloride the reaction proceeds on the thiocarbonyl group, while the morpholine residue is replaced by ethoxy group under formation of the respective 0-ethyl monothiocarbamate. On treatment of the studied thioureas with bromine in chloroform it was found that only the compounds with aromatic residue were reactive. While N'-phenyl derivatives are oxidized to the respec­tive ureas, N',N'-diphenylthioureas undergo intramolecular electrophilic aromatic substitution to give benzothiazoline derivatives.

Full paper in Portable Document Format: 414a519.pdf


Chemical Papers 41 (4) 519–526 (1987)

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