Abstract
The interaction of the sodium salts of 3-(1-adamantyl)-1-hydroxy-1-propen-3-one and 4-(1-adamantyl)-1-hydroxy-1-buten-3-one with hydroxylamine, hydrazine, and guanidine leads to the synthesis of 5-(1-adamantyl)-5-hydroxy- and 5-(1-adamantylmethyl)-5-hydroxy-Δ2-isoxazolines, 3-(1-adamantyl)- and 3-(1-adamantylmethyl)pyrazoles, 3-(1-adamantyl)-2-phenylpyrazole, and 4-(1-adamantyl)-2-amino- and 4-(1-adamantylmethyl)-2-aminopyrimidines.
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Makarova, N.V., Zemtsova, M.N. & Moiseev, I.K. Syntheses of Heterocycles from the Sodium Salts of 3-(1-Adamantyl)-1-hydroxy-1-propen-3-one and 4-(1-Adamantyl)-1-hydroxy-1-buten-3-one. Chemistry of Heterocyclic Compounds 37, 840–843 (2001). https://doi.org/10.1023/A:1012443306632
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DOI: https://doi.org/10.1023/A:1012443306632