Methyl 3,5-dioxohexanoate (1) reacts with hydrazines (2) in methanol or acetic acid to give a mixture of the isomeric pyrazolylacetates (3) and (4), whose molar ratio depends on the solvent and hydrazine. 2,2-Dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione (5) reacts chemoselectively with hydrazines to give the 5-pyrazolylacetates (3) as the only reaction products.
Chemoselective synthesis of 3-and 5-pyrazolylacetates / C. Vicentini, M. Manfrini, M. Mazzanti, M. Manferdini, C. F. Morelli, A. Veronese. - In: HETEROCYCLES. - ISSN 0385-5414. - 53:6(2000), pp. 1285-1292.
Chemoselective synthesis of 3-and 5-pyrazolylacetates
C. F. Morelli;
2000
Abstract
Methyl 3,5-dioxohexanoate (1) reacts with hydrazines (2) in methanol or acetic acid to give a mixture of the isomeric pyrazolylacetates (3) and (4), whose molar ratio depends on the solvent and hydrazine. 2,2-Dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione (5) reacts chemoselectively with hydrazines to give the 5-pyrazolylacetates (3) as the only reaction products.
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