I. B. Chernikova, A. N. Lobov, E. S. Meshcheryakova, L. M. Khalilov, M. S. Yunusov, “An unexpected product of the reaction between <i>N</i>-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas”, Mendeleev Commun., 2023, Volume 33, Issue 5,Pages <nobr>714

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Communications

An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas

I. B. Chernikova^a, A. N. Lobov^a, E. S. Meshcheryakova^b, L. M. Khalilov^b, M. S. Yunusov^a

^a Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
^b Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: 5-Isothiocyanato-6-methylpyrimidine-2,4(1H,3H)-dione was formed in the course of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and a series of thioureas in MeOH in the presence of Et₃N. The transformation follows the Hoffman rearrangement mechanism, with the nitrile N-oxide being the key intermediate.

Keywords: 6-methyluracil, N-hydroxy-6-methyluracil-5-carboximidoyl chloride, nitrile N-oxides, thioureas, isothiocyanates.

Language: English

DOI: 10.1016/j.mencom.2023.09.039

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