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

ABSTRACT: 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.

SUBMITTER: Kurpet MK

PROVIDER: S-EPMC3740504 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Kurpet Marta K MK Dąbrowska Aleksandra A Jarosz Małgorzata M MM Kajewska-Kania Katarzyna K Kuźnik Nikodem N Suwiński Jerzy W JW

Beilstein journal of organic chemistry 20130730

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. ...[more]

PMID: 23946851

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