Abstract
N-(2-Oxoalkyl)-2-chloroacetohydroxamic acids were obtained by acylation of 1,2-hydroxylamino ketones with chloroacetyl chloride. Their reaction with urotropin and sodium azide gives urotropinium salts and acetoxyhydroxamic acid azides. 1-Hydroxy-2-oxo-1,2,3,6-tetrahydropyrazines were obtained by treating N-(2-oxoalkyl)-2-chloroacetohydroxyamic acids with ammonia, and also by reacting the urotropinium salts and azides of acetohydroxamic acids with hydrochloric acid and triphenylphosphine, respectively. The reaction of N-(1-methyl-2-oxo-2-phenylethyl)-2-chloroacetohydroxamic acid with urotropin in an acid medium leads to the formation of 6-methyl-2-oxo-5-phenyl-1,2-dihydropyrazine.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 509–513, April, 1986.
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Reznikova, T.I., Tikhonov, A.Y. & Volodarskii, L.B. Preparation of derivatives of 1,2-dihydro- and 1,2,3,6-tetrahydropyrazinones from acylated 1,2-hydroxylamino ketones. Chem Heterocycl Compd 22, 417–421 (1986). https://doi.org/10.1007/BF00542782
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DOI: https://doi.org/10.1007/BF00542782