Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the syntheti...

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Detalles Bibliográficos
Autores principales: Demjén, András, Gyuris, Márió, Wölfling, János, Puskás, László G, Kanizsai, Iván
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222397/
https://www.ncbi.nlm.nih.gov/pubmed/25383103
http://dx.doi.org/10.3762/bjoc.10.243
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author Demjén, András
Gyuris, Márió
Wölfling, János
Puskás, László G
Kanizsai, Iván
author_facet Demjén, András
Gyuris, Márió
Wölfling, János
Puskás, László G
Kanizsai, Iván
author_sort Demjén, András
collection PubMed
description 5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.
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spelling pubmed-42223972014-11-07 Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach Demjén, András Gyuris, Márió Wölfling, János Puskás, László G Kanizsai, Iván Beilstein J Org Chem Full Research Paper 5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%. Beilstein-Institut 2014-10-08 /pmc/articles/PMC4222397/ /pubmed/25383103 http://dx.doi.org/10.3762/bjoc.10.243 Text en Copyright © 2014, Demjén et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
Demjén, András
Gyuris, Márió
Wölfling, János
Puskás, László G
Kanizsai, Iván
Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
title Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
title_full Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
title_fullStr Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
title_full_unstemmed Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
title_short Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
title_sort facile synthesis of 1h-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222397/
https://www.ncbi.nlm.nih.gov/pubmed/25383103
http://dx.doi.org/10.3762/bjoc.10.243
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