Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding...

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Detalles Bibliográficos
Autores principales: Datterl, Barbara, Tröstner, Nicole, Kucharski, Dorota, Holzer, Wolfgang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257680/
https://www.ncbi.nlm.nih.gov/pubmed/20877210
http://dx.doi.org/10.3390/molecules15096106
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author Datterl, Barbara
Tröstner, Nicole
Kucharski, Dorota
Holzer, Wolfgang
author_facet Datterl, Barbara
Tröstner, Nicole
Kucharski, Dorota
Holzer, Wolfgang
author_sort Datterl, Barbara
collection PubMed
description The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K(2)CO(3)/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations ((1)H, (13)C, (15)N) of the ring systems and their precursors are presented.
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spelling pubmed-62576802018-12-06 Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data Datterl, Barbara Tröstner, Nicole Kucharski, Dorota Holzer, Wolfgang Molecules Article The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K(2)CO(3)/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations ((1)H, (13)C, (15)N) of the ring systems and their precursors are presented. MDPI 2010-09-01 /pmc/articles/PMC6257680/ /pubmed/20877210 http://dx.doi.org/10.3390/molecules15096106 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Datterl, Barbara
Tröstner, Nicole
Kucharski, Dorota
Holzer, Wolfgang
Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
title Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
title_full Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
title_fullStr Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
title_full_unstemmed Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
title_short Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
title_sort heterocyclic analogues of xanthone and xanthione. 1h-pyrano[2,3-c:6,5-c]dipyrazol-4(7h)-ones and thiones: synthesis and nmr data
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257680/
https://www.ncbi.nlm.nih.gov/pubmed/20877210
http://dx.doi.org/10.3390/molecules15096106
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