Electrosynthesis of pyrazole-4-carboxylic acids by oxidation of 4-formylpyrazoles on NiO(OH)-electrode in aqueous alkaline solution |
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Authors: | B. V. Lyalin V. A. Petrosyan |
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Affiliation: | 1156. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
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Abstract: | Electrochemical oxidation of di- and trisubstituted 4-formylpyrazoles on a Ni-anode in aqueous alkali led to the formation of the corresponding pyrazole-4-carboxylic acid in 60–90% yields. The yields of the target products depend on position of substituent in the pyrazole ring and are decreased in the following sequence of substituent at position 1 Me > Et > Ph, as well as when the aqueous medium was replaced with aqueous alcohol (50% ButOH). Oxidation of 4-formylpyrazoles containing Me groups at the carbon atoms of the pyrazole ring led, to monoacids and also pyrazoledicarboxylic acids in small (1.5–14%) amounts; the latter were the oxidation products of the aldehyde and the Me groups. |
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