Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach

A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-but...

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Autores principales: Palka, Barbara, Di Capua, Angela, Anzini, Maurizio, Vilkauskaité, Gyté, Šačkus, Algirdas, Holzer, Wolfgang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142841/
https://www.ncbi.nlm.nih.gov/pubmed/25161734
http://dx.doi.org/10.3762/bjoc.10.183
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author Palka, Barbara
Di Capua, Angela
Anzini, Maurizio
Vilkauskaité, Gyté
Šačkus, Algirdas
Holzer, Wolfgang
author_facet Palka, Barbara
Di Capua, Angela
Anzini, Maurizio
Vilkauskaité, Gyté
Šačkus, Algirdas
Holzer, Wolfgang
author_sort Palka, Barbara
collection PubMed
description A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compounds in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations ((1)H, (13)C, (15)N and (19)F) were undertaken with all obtained products.
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spelling pubmed-41428412014-08-26 Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach Palka, Barbara Di Capua, Angela Anzini, Maurizio Vilkauskaité, Gyté Šačkus, Algirdas Holzer, Wolfgang Beilstein J Org Chem Full Research Paper A straightforward synthesis of 6-substituted 1-phenyl-3-trifluoromethyl-1H-pyrazolo[4,3-c]pyridines and the corresponding 5-oxides is presented. Hence, microwave-assisted treatment of 5-chloro-1-phenyl-3-trifluoromethylpyrazole-4-carbaldehyde with various terminal alkynes in the presence of tert-butylamine under Sonogashira-type cross-coupling conditions affords the former title compounds in a one-pot multicomponent procedure. Oximes derived from (intermediate) 5-alkynyl-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehydes were transformed into the corresponding 1H-pyrazolo[4,3-c]pyridine 5-oxides by silver triflate-catalyzed cyclization. Detailed NMR spectroscopic investigations ((1)H, (13)C, (15)N and (19)F) were undertaken with all obtained products. Beilstein-Institut 2014-07-31 /pmc/articles/PMC4142841/ /pubmed/25161734 http://dx.doi.org/10.3762/bjoc.10.183 Text en Copyright © 2014, Palka et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Palka, Barbara
Di Capua, Angela
Anzini, Maurizio
Vilkauskaité, Gyté
Šačkus, Algirdas
Holzer, Wolfgang
Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
title Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
title_full Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
title_fullStr Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
title_full_unstemmed Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
title_short Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
title_sort synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142841/
https://www.ncbi.nlm.nih.gov/pubmed/25161734
http://dx.doi.org/10.3762/bjoc.10.183
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