Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles

Despite the pharmacological potential of the pyrazolo[3,4-c]pyrazoles, only a few methods of preparation and direct functionalization of this moiety have been described. We report herein a convenient design of new pyrazolo[3,4-c]pyrazoles with a high therapeutic impact. The effective chosen strategy...

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Autores principales: Ostache, Nicu-Cosmin, Hiebel, Marie-Aude, Fînaru, Adriana-Luminiţa, Allouchi, Hassan, Guillaumet, Gérald, Suzenet, Franck
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695482/
https://www.ncbi.nlm.nih.gov/pubmed/35423466
http://dx.doi.org/10.1039/d1ra00314c
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author Ostache, Nicu-Cosmin
Hiebel, Marie-Aude
Fînaru, Adriana-Luminiţa
Allouchi, Hassan
Guillaumet, Gérald
Suzenet, Franck
author_facet Ostache, Nicu-Cosmin
Hiebel, Marie-Aude
Fînaru, Adriana-Luminiţa
Allouchi, Hassan
Guillaumet, Gérald
Suzenet, Franck
author_sort Ostache, Nicu-Cosmin
collection PubMed
description Despite the pharmacological potential of the pyrazolo[3,4-c]pyrazoles, only a few methods of preparation and direct functionalization of this moiety have been described. We report herein a convenient design of new pyrazolo[3,4-c]pyrazoles with a high therapeutic impact. The effective chosen strategy consists of hydrazine condensations and C–N Ullmann-type cross-coupling reactions with microwave activation. Moreover, chemoselective bromination of the newly formed bipyrazoles followed by Suzuki–Miyaura cross-coupling reactions allowed the synthesis of a variety of modulated heterobicycles.
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spelling pubmed-86954822022-04-13 Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles Ostache, Nicu-Cosmin Hiebel, Marie-Aude Fînaru, Adriana-Luminiţa Allouchi, Hassan Guillaumet, Gérald Suzenet, Franck RSC Adv Chemistry Despite the pharmacological potential of the pyrazolo[3,4-c]pyrazoles, only a few methods of preparation and direct functionalization of this moiety have been described. We report herein a convenient design of new pyrazolo[3,4-c]pyrazoles with a high therapeutic impact. The effective chosen strategy consists of hydrazine condensations and C–N Ullmann-type cross-coupling reactions with microwave activation. Moreover, chemoselective bromination of the newly formed bipyrazoles followed by Suzuki–Miyaura cross-coupling reactions allowed the synthesis of a variety of modulated heterobicycles. The Royal Society of Chemistry 2021-03-05 /pmc/articles/PMC8695482/ /pubmed/35423466 http://dx.doi.org/10.1039/d1ra00314c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Ostache, Nicu-Cosmin
Hiebel, Marie-Aude
Fînaru, Adriana-Luminiţa
Allouchi, Hassan
Guillaumet, Gérald
Suzenet, Franck
Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
title Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
title_full Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
title_fullStr Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
title_full_unstemmed Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
title_short Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
title_sort access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695482/
https://www.ncbi.nlm.nih.gov/pubmed/35423466
http://dx.doi.org/10.1039/d1ra00314c
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