Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles

A method for the synthesis of N-aryl-C-nitroazoles is presented. A coupling reaction between variously substituted arylboronic acids and 3(5)-nitro-1H-pyrazole catalyzed by copper salt has been carried out in methanol in the presence of sodium hydroxide to afford the desired N-aryl-C-nitroazoles in...

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Autores principales: Kurpet, Marta K, Dąbrowska, Aleksandra, Jarosz, Małgorzata M, Kajewska-Kania, Katarzyna, Kuźnik, Nikodem, Suwiński, Jerzy W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740504/
https://www.ncbi.nlm.nih.gov/pubmed/23946851
http://dx.doi.org/10.3762/bjoc.9.173
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author Kurpet, Marta K
Dąbrowska, Aleksandra
Jarosz, Małgorzata M
Kajewska-Kania, Katarzyna
Kuźnik, Nikodem
Suwiński, Jerzy W
author_facet Kurpet, Marta K
Dąbrowska, Aleksandra
Jarosz, Małgorzata M
Kajewska-Kania, Katarzyna
Kuźnik, Nikodem
Suwiński, Jerzy W
author_sort Kurpet, Marta K
collection PubMed
description A method for the synthesis of N-aryl-C-nitroazoles is presented. A coupling reaction between variously substituted arylboronic acids and 3(5)-nitro-1H-pyrazole catalyzed by copper salt has been carried out in methanol in the presence of sodium hydroxide to afford the desired N-aryl-C-nitroazoles in good yields. This synthetic route has also been successfully applied to obtain N-phenyl derivatives of 4-nitropyrazole, 2-nitroimidazole, 4(5)-nitroimidazole and 3-nitro-1,2,4-triazole.
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spelling pubmed-37405042013-08-14 Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles Kurpet, Marta K Dąbrowska, Aleksandra Jarosz, Małgorzata M Kajewska-Kania, Katarzyna Kuźnik, Nikodem Suwiński, Jerzy W Beilstein J Org Chem Full Research Paper A method for the synthesis of N-aryl-C-nitroazoles is presented. A coupling reaction between variously substituted arylboronic acids and 3(5)-nitro-1H-pyrazole catalyzed by copper salt has been carried out in methanol in the presence of sodium hydroxide to afford the desired N-aryl-C-nitroazoles in good yields. This synthetic route has also been successfully applied to obtain N-phenyl derivatives of 4-nitropyrazole, 2-nitroimidazole, 4(5)-nitroimidazole and 3-nitro-1,2,4-triazole. Beilstein-Institut 2013-07-30 /pmc/articles/PMC3740504/ /pubmed/23946851 http://dx.doi.org/10.3762/bjoc.9.173 Text en Copyright © 2013, Kurpet 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
Kurpet, Marta K
Dąbrowska, Aleksandra
Jarosz, Małgorzata M
Kajewska-Kania, Katarzyna
Kuźnik, Nikodem
Suwiński, Jerzy W
Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles
title Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles
title_full Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles
title_fullStr Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles
title_full_unstemmed Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles
title_short Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles
title_sort coupling of c-nitro-nh-azoles with arylboronic acids. a route to n-aryl-c-nitroazoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740504/
https://www.ncbi.nlm.nih.gov/pubmed/23946851
http://dx.doi.org/10.3762/bjoc.9.173
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