An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones

Dialkyl 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates are readily obtained by the reaction of 5-hydroxypyrazole-4-carboxylates in refluxing thionyl chloride. The obtained diesters can be transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent d...

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Autores principales: Eller, Gernot A, Vilkauskaitė, Gytė, Šačkus, Algirdas, Martynaitis, Vytas, Mamuye, Ashenafi Damtew, Pace, Vittorio, Holzer, Wolfgang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009192/
https://www.ncbi.nlm.nih.gov/pubmed/29977396
http://dx.doi.org/10.3762/bjoc.14.110
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author Eller, Gernot A
Vilkauskaitė, Gytė
Šačkus, Algirdas
Martynaitis, Vytas
Mamuye, Ashenafi Damtew
Pace, Vittorio
Holzer, Wolfgang
author_facet Eller, Gernot A
Vilkauskaitė, Gytė
Šačkus, Algirdas
Martynaitis, Vytas
Mamuye, Ashenafi Damtew
Pace, Vittorio
Holzer, Wolfgang
author_sort Eller, Gernot A
collection PubMed
description Dialkyl 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates are readily obtained by the reaction of 5-hydroxypyrazole-4-carboxylates in refluxing thionyl chloride. The obtained diesters can be transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent decarboxylation. Detailed NMR spectroscopic investigations ((1)H, (13)C, (15)N) were undertaken with all products prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis.
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spelling pubmed-60091922018-07-05 An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones Eller, Gernot A Vilkauskaitė, Gytė Šačkus, Algirdas Martynaitis, Vytas Mamuye, Ashenafi Damtew Pace, Vittorio Holzer, Wolfgang Beilstein J Org Chem Full Research Paper Dialkyl 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates are readily obtained by the reaction of 5-hydroxypyrazole-4-carboxylates in refluxing thionyl chloride. The obtained diesters can be transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent decarboxylation. Detailed NMR spectroscopic investigations ((1)H, (13)C, (15)N) were undertaken with all products prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis. Beilstein-Institut 2018-06-04 /pmc/articles/PMC6009192/ /pubmed/29977396 http://dx.doi.org/10.3762/bjoc.14.110 Text en Copyright © 2018, Eller 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), 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
Eller, Gernot A
Vilkauskaitė, Gytė
Šačkus, Algirdas
Martynaitis, Vytas
Mamuye, Ashenafi Damtew
Pace, Vittorio
Holzer, Wolfgang
An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
title An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
title_full An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
title_fullStr An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
title_full_unstemmed An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
title_short An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones
title_sort unusual thionyl chloride-promoted c−c bond formation to obtain 4,4'-bipyrazolones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009192/
https://www.ncbi.nlm.nih.gov/pubmed/29977396
http://dx.doi.org/10.3762/bjoc.14.110
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