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1973•Bulletin of the Chemical Society of JapanRequires access

Synthesis of Pyrazole Derivatives Using 1-Benzoyl-1-phenylhydrazine

ABDOU AHMED EL‐SAYED, Masaki Ohta

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Abstract

Abstract Condensation of 1-benzoyl-1-phenylhydrazine (I) with β-ketoesters and β-diketones was investigated. Reaction of I with ethyl acetoacetate, ethyl benzoylacetate and diethyl acetonedicarboxylate in the presence of phosphorus pentoxide afforded the corresponding hydrazones which were easily cyclized by sodium hydroxide to give pyrazole derivatives. Reaction of I with acetylacetone proceeded to give hydrazone without condensing agent. 4-Carboxy-1,5-diphenylpyrazol-3-ylacetic acid and its mono- and diester were also prepared.

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What this paper is about

Abstract Condensation of 1-benzoyl-1-phenylhydrazine (I) with β-ketoesters and β-diketones was investigated. Reaction of I with ethyl acetoacetate, ethyl benzoylacetate and diethyl acetonedicarboxylate in the presence of phosphorus pentoxide afforded the corresponding hydrazones which were easily cyclized by sodium hydroxide to give pyrazole derivatives. Reaction of I with acetylacetone proceeded to give hydrazone without condensing agent. 4-Carboxy-1,5-diphenylpyrazol-3-ylacetic acid and its mono- and diester were also prepared.

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Available abstract

Abstract Condensation of 1-benzoyl-1-phenylhydrazine (I) with β-ketoesters and β-diketones was investigated. Reaction of I with ethyl acetoacetate, ethyl benzoylacetate and diethyl acetonedicarboxylate in the presence of phosphorus pentoxide afforded the corresponding hydrazones which were easily cyclized by sodium hydroxide to give pyrazole derivatives. Reaction of I with acetylacetone proceeded to give hydrazone without condensing agent. 4-Carboxy-1,5-diphenylpyrazol-3-ylacetic acid and its mono- and diester were also prepared.

Key concepts: Chemistry, Phenylhydrazine, Ethyl acetoacetate, Acetylacetone, Pyrazole, Hydrazone, Pentoxide, Sodium hydroxide

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