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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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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. |
format | Online Article Text |
id | pubmed-6643981 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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