Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones

The first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide...

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Autores principales: Ejjoummany, Abdelaziz, Elie, Jonathan, El Hakmaoui, Ahmed, Akssira, Mohamed, Routier, Sylvain, Buron, Frédéric
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10421423/
https://www.ncbi.nlm.nih.gov/pubmed/37570778
http://dx.doi.org/10.3390/molecules28155811
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author Ejjoummany, Abdelaziz
Elie, Jonathan
El Hakmaoui, Ahmed
Akssira, Mohamed
Routier, Sylvain
Buron, Frédéric
author_facet Ejjoummany, Abdelaziz
Elie, Jonathan
El Hakmaoui, Ahmed
Akssira, Mohamed
Routier, Sylvain
Buron, Frédéric
author_sort Ejjoummany, Abdelaziz
collection PubMed
description The first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki–Miyaura or Buchwald–Hartwig coupling reactions in C-6 position was investigated from 6-chloropyrrolo[3,4-c]pyrazole-4,6-(2H,5H)–diones. This method provides novel access to various 1,6 di-substituted pyrrolo[3,4-c] pyrazole-4,6-(2H,5H)–diones.
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spelling pubmed-104214232023-08-12 Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones Ejjoummany, Abdelaziz Elie, Jonathan El Hakmaoui, Ahmed Akssira, Mohamed Routier, Sylvain Buron, Frédéric Molecules Article The first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki–Miyaura or Buchwald–Hartwig coupling reactions in C-6 position was investigated from 6-chloropyrrolo[3,4-c]pyrazole-4,6-(2H,5H)–diones. This method provides novel access to various 1,6 di-substituted pyrrolo[3,4-c] pyrazole-4,6-(2H,5H)–diones. MDPI 2023-08-01 /pmc/articles/PMC10421423/ /pubmed/37570778 http://dx.doi.org/10.3390/molecules28155811 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ejjoummany, Abdelaziz
Elie, Jonathan
El Hakmaoui, Ahmed
Akssira, Mohamed
Routier, Sylvain
Buron, Frédéric
Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones
title Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones
title_full Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones
title_fullStr Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones
title_full_unstemmed Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones
title_short Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones
title_sort access and modulation of substituted pyrrolo[3,4-c]pyrazole-4,6-(2h,5h)-diones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10421423/
https://www.ncbi.nlm.nih.gov/pubmed/37570778
http://dx.doi.org/10.3390/molecules28155811
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