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Synthesis and addition-nucleophilic reactions of 2-chloro-3-pyridyl and 2,6-dimethyl-4-chloro-3-pyridyl isocyanates

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

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, P. J. Šafárik University, CS-041 67 Košice


Abstract: 2-Chloro-3-pyridyl isocyanate and 2,6-dimethyl-4-chloro-3-pyridyl isocyanate, prepared by decomposition of the corresponding acyl azides, react with amines, benzyl alcohol, and phenylmethanethiol under formation of the respective ureas and esters of carbamic acids, respectively. On heating in solvents of different polarities, in alkaline or acidic media intramolecular cyclization of the obtained products to derivatives of pyridoimidazole and pyridooxazole does not proceed, while photolysis of N-phenyl-N'-(2,6-dimethyl-4-chloro-3-pyridyl)urea affords a pyridoimidazole derivative. Treatment of the prepared ureas with potassium thiocyanate in acidic medium results in 2-arninopyrido[3,2-d|thiazole and 2-amino-4,6-dimethylpyrido[3,4-d|thiazole.

Full paper in Portable Document Format: 415a683.pdf


Chemical Papers 41 (5) 683–691 (1987)

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