The thermal isomerisation of isoxazol-5-ylhydrazines (I) led to 1-aminopyrazolin-5-ones (II), 4-aminopyrazolin-5-ones (III), and 1,2,4-triazin-6-ones (IV), in ratios depending on the nature of the substituents and the solvents used. A reaction mechanism involving a bicyclic intermediate, is suggested on the basis of the behaviour of isoxazolyl hydrazines methylated on the hydrazine moiety towards heating. Heating the methylated isoxazolylhydrazines (IXg and h) afforded the corresponding azirinecarbohydrazides (XII).
Adembri, G., Camparini, A., Ponticelli, F., Tedeschi, P. (1977). Thermally Induced isomerisation of Isoxazol-5-ylhydrazines. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I, 9, 971-979 [10.1039/p19770000971].
Thermally Induced isomerisation of Isoxazol-5-ylhydrazines
Adembri, Giorgio;Camparini, Alfredo;Ponticelli, Fabio;
1977-01-01
Abstract
The thermal isomerisation of isoxazol-5-ylhydrazines (I) led to 1-aminopyrazolin-5-ones (II), 4-aminopyrazolin-5-ones (III), and 1,2,4-triazin-6-ones (IV), in ratios depending on the nature of the substituents and the solvents used. A reaction mechanism involving a bicyclic intermediate, is suggested on the basis of the behaviour of isoxazolyl hydrazines methylated on the hydrazine moiety towards heating. Heating the methylated isoxazolylhydrazines (IXg and h) afforded the corresponding azirinecarbohydrazides (XII).
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https://hdl.handle.net/11365/6535
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