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Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles.

ABSTRACT: The pyrazole scaffold is one of the most prevalent and important tool in medicinal chemistry. Here, we report a method for preparing 3,5-diarylpyrazoles in good to excellent yield by reacting hydrazones of aryl aldehydes with substituted acetophenones in ethanol in the presence of dimethyl sulfoxide/cat. I₂/cat. HCl. The reverse process, reacting hydrazones of substituted acetophenones with aryl aldehydes under the same conditions, also provides 3,5-diarylpyrazoles in good to excellent yields. Reaction of hydrazones of aldehydes with 2'-aryloxy ketones in the presence of cat. HCl in ethanol and the catalyst-free reaction of phenacyl bromides with hydrazones of aldehydes in ethanol also gave good to excellent yields of 3,5-diarylpyrazoles.

SUBMITTER: Mohamady S

PROVIDER: S-EPMC6643981 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles.

Mohamady Samy S Kralt Braden B Samwel Shery K SK Taylor Scott D SD

ACS omega 20181115 11

The pyrazole scaffold is one of the most prevalent and important tool in medicinal chemistry. Here, we report a method for preparing 3,5-diarylpyrazoles in good to excellent yield by reacting hydrazones of aryl aldehydes with substituted acetophenones in ethanol in the presence of dimethyl sulfoxide/cat. I<sub>2</sub>/cat. HCl. The reverse process, reacting hydrazones of substituted acetophenones with aryl aldehydes under the same conditions, also provides 3,5-diarylpyrazoles in good to excellen ...[more]

PMID: 31458212

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