One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene

[Image: see text] A synthetically useful approach for one-pot preparation of 1-aryl-3-trifluoromethylpyrazoles using in situ generated nitrile imines and mercaptoacetaldehyde applied as 1 equiv of acetylene is presented. This protocol comprises (3 + 3)-annulation of the mentioned reagents to form 5,...

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Autores principales: Świątek, Kamil, Utecht-Jarzyńska, Greta, Palusiak, Marcin, Ma, Jun-An, Jasiński, Marcin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10294255/
https://www.ncbi.nlm.nih.gov/pubmed/37309990
http://dx.doi.org/10.1021/acs.orglett.3c01437
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author Świątek, Kamil
Utecht-Jarzyńska, Greta
Palusiak, Marcin
Ma, Jun-An
Jasiński, Marcin
author_facet Świątek, Kamil
Utecht-Jarzyńska, Greta
Palusiak, Marcin
Ma, Jun-An
Jasiński, Marcin
author_sort Świątek, Kamil
collection PubMed
description [Image: see text] A synthetically useful approach for one-pot preparation of 1-aryl-3-trifluoromethylpyrazoles using in situ generated nitrile imines and mercaptoacetaldehyde applied as 1 equiv of acetylene is presented. This protocol comprises (3 + 3)-annulation of the mentioned reagents to form 5,6-dihydro-5-hydroxy-4H-1,3,4-thiadiazine, followed by cascade dehydration/ring contraction reactions with p-TsCl. In addition, representative nonfluorinated analogues functionalized with Ph, Ac, and CO(2)Et groups at the C(3)-position of the pyrazole ring were also prepared by the devised method.
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spelling pubmed-102942552023-06-28 One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene Świątek, Kamil Utecht-Jarzyńska, Greta Palusiak, Marcin Ma, Jun-An Jasiński, Marcin Org Lett [Image: see text] A synthetically useful approach for one-pot preparation of 1-aryl-3-trifluoromethylpyrazoles using in situ generated nitrile imines and mercaptoacetaldehyde applied as 1 equiv of acetylene is presented. This protocol comprises (3 + 3)-annulation of the mentioned reagents to form 5,6-dihydro-5-hydroxy-4H-1,3,4-thiadiazine, followed by cascade dehydration/ring contraction reactions with p-TsCl. In addition, representative nonfluorinated analogues functionalized with Ph, Ac, and CO(2)Et groups at the C(3)-position of the pyrazole ring were also prepared by the devised method. American Chemical Society 2023-06-13 /pmc/articles/PMC10294255/ /pubmed/37309990 http://dx.doi.org/10.1021/acs.orglett.3c01437 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Świątek, Kamil
Utecht-Jarzyńska, Greta
Palusiak, Marcin
Ma, Jun-An
Jasiński, Marcin
One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene
title One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene
title_full One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene
title_fullStr One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene
title_full_unstemmed One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene
title_short One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene
title_sort one-pot synthesis of 1-aryl-3-trifluoromethylpyrazoles using nitrile imines and mercaptoacetaldehyde as a surrogate of acetylene
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10294255/
https://www.ncbi.nlm.nih.gov/pubmed/37309990
http://dx.doi.org/10.1021/acs.orglett.3c01437
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