Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

Fused pyrazole ring systems are common structural motifs of numerous pharmaceutically important compounds. Nevertheless, access to derivatives of the aromatic 2H-furo[2,3-c]pyrazole ring system is still quite limited, and their chemistry and functional properties remain largely underexplored. The cu...

Descripción completa

Detalles Bibliográficos
Autores principales: Milišiūnaitė, Vaida, Paulavičiūtė, Rūta, Arbačiauskienė, Eglė, Martynaitis, Vytas, Holzer, Wolfgang, Šačkus, Algirdas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6423569/
https://www.ncbi.nlm.nih.gov/pubmed/30931008
http://dx.doi.org/10.3762/bjoc.15.62
_version_ 1783404549493489664
author Milišiūnaitė, Vaida
Paulavičiūtė, Rūta
Arbačiauskienė, Eglė
Martynaitis, Vytas
Holzer, Wolfgang
Šačkus, Algirdas
author_facet Milišiūnaitė, Vaida
Paulavičiūtė, Rūta
Arbačiauskienė, Eglė
Martynaitis, Vytas
Holzer, Wolfgang
Šačkus, Algirdas
author_sort Milišiūnaitė, Vaida
collection PubMed
description Fused pyrazole ring systems are common structural motifs of numerous pharmaceutically important compounds. Nevertheless, access to derivatives of the aromatic 2H-furo[2,3-c]pyrazole ring system is still quite limited, and their chemistry and functional properties remain largely underexplored. The current study investigates routes to construct this system from easily accessible starting materials using metal-catalyzed reactions. A simple and efficient procedure to access the 2H-furo[2,3-c]pyrazole ring system was developed by employing the silver(I) ion-mediated ring-closure reaction of 4-alkynyl-3-hydroxy-1-phenyl-1H-pyrazoles as a key step. The required intermediate hydroxyalkynyl substrates for this reaction were prepared by a Pd-catalyzed coupling of 4-iodo-1-phenyl-1H-pyrazol-3-ol with ethyne derivatives. The structures of the obtained target compounds were unequivocally confirmed by detailed (1)H, (13)C and (15)N NMR spectroscopic experiments, HRMS and a single-crystal X-ray diffraction analyses. This silver(I)-mediated 5-endo-dig cyclization of readily available 4-alkynyl-3-hydroxy-1H-pyrazoles can be used as an efficient method to access many novel 2,5-disubstituted 2H-furo[2,3-c]pyrazoles.
format Online
Article
Text
id pubmed-6423569
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-64235692019-03-29 Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction Milišiūnaitė, Vaida Paulavičiūtė, Rūta Arbačiauskienė, Eglė Martynaitis, Vytas Holzer, Wolfgang Šačkus, Algirdas Beilstein J Org Chem Full Research Paper Fused pyrazole ring systems are common structural motifs of numerous pharmaceutically important compounds. Nevertheless, access to derivatives of the aromatic 2H-furo[2,3-c]pyrazole ring system is still quite limited, and their chemistry and functional properties remain largely underexplored. The current study investigates routes to construct this system from easily accessible starting materials using metal-catalyzed reactions. A simple and efficient procedure to access the 2H-furo[2,3-c]pyrazole ring system was developed by employing the silver(I) ion-mediated ring-closure reaction of 4-alkynyl-3-hydroxy-1-phenyl-1H-pyrazoles as a key step. The required intermediate hydroxyalkynyl substrates for this reaction were prepared by a Pd-catalyzed coupling of 4-iodo-1-phenyl-1H-pyrazol-3-ol with ethyne derivatives. The structures of the obtained target compounds were unequivocally confirmed by detailed (1)H, (13)C and (15)N NMR spectroscopic experiments, HRMS and a single-crystal X-ray diffraction analyses. This silver(I)-mediated 5-endo-dig cyclization of readily available 4-alkynyl-3-hydroxy-1H-pyrazoles can be used as an efficient method to access many novel 2,5-disubstituted 2H-furo[2,3-c]pyrazoles. Beilstein-Institut 2019-03-14 /pmc/articles/PMC6423569/ /pubmed/30931008 http://dx.doi.org/10.3762/bjoc.15.62 Text en Copyright © 2019, Milišiūnaitė et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Milišiūnaitė, Vaida
Paulavičiūtė, Rūta
Arbačiauskienė, Eglė
Martynaitis, Vytas
Holzer, Wolfgang
Šačkus, Algirdas
Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction
title Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction
title_full Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction
title_fullStr Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction
title_full_unstemmed Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction
title_short Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction
title_sort synthesis of 2h-furo[2,3-c]pyrazole ring systems through silver(i) ion-mediated ring-closure reaction
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6423569/
https://www.ncbi.nlm.nih.gov/pubmed/30931008
http://dx.doi.org/10.3762/bjoc.15.62
work_keys_str_mv AT milisiunaitevaida synthesisof2hfuro23cpyrazoleringsystemsthroughsilveriionmediatedringclosurereaction
AT paulaviciuteruta synthesisof2hfuro23cpyrazoleringsystemsthroughsilveriionmediatedringclosurereaction
AT arbaciauskieneegle synthesisof2hfuro23cpyrazoleringsystemsthroughsilveriionmediatedringclosurereaction
AT martynaitisvytas synthesisof2hfuro23cpyrazoleringsystemsthroughsilveriionmediatedringclosurereaction
AT holzerwolfgang synthesisof2hfuro23cpyrazoleringsystemsthroughsilveriionmediatedringclosurereaction
AT sackusalgirdas synthesisof2hfuro23cpyrazoleringsystemsthroughsilveriionmediatedringclosurereaction