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

[Image: see text] 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...

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Autores principales: Mohamady, Samy, Kralt, Braden, Samwel, Shery K., Taylor, Scott D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6643981/
https://www.ncbi.nlm.nih.gov/pubmed/31458212
http://dx.doi.org/10.1021/acsomega.8b02304
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author Mohamady, Samy
Kralt, Braden
Samwel, Shery K.
Taylor, Scott D.
author_facet Mohamady, Samy
Kralt, Braden
Samwel, Shery K.
Taylor, Scott D.
author_sort Mohamady, Samy
collection PubMed
description [Image: see text] 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(2)/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.
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spelling pubmed-66439812019-08-27 Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles Mohamady, Samy Kralt, Braden Samwel, Shery K. Taylor, Scott D. ACS Omega [Image: see text] 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(2)/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. American Chemical Society 2018-11-15 /pmc/articles/PMC6643981/ /pubmed/31458212 http://dx.doi.org/10.1021/acsomega.8b02304 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Mohamady, Samy
Kralt, Braden
Samwel, Shery K.
Taylor, Scott D.
Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
title Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
title_full Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
title_fullStr Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
title_full_unstemmed Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
title_short Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
title_sort efficient one-pot, two-component modular synthesis of 3,5-disubstituted pyrazoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6643981/
https://www.ncbi.nlm.nih.gov/pubmed/31458212
http://dx.doi.org/10.1021/acsomega.8b02304
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