Beilstein J. Org. Chem.2013,9, 1517–1525, doi:10.3762/bjoc.9.173
Materials, Polish Academy of Sciences, M. Curie-Skłodowskiej 34, Zabrze 41-819, Poland 10.3762/bjoc.9.173 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
.
Keywords: arylboronic acids; C-nitroazoles; coupling; N-arylation; N-aryl-C-nitroazoles; Introduction
The nitroazoles constitute a class of compounds with a broad spectrum of useful properties. They have found applications in agrochemicals as plant-growth regulators [1], herbicides or insecticides [2], in
PDF
Graphical Abstract
Scheme 1:
Methods of synthesis of 3-nitro-1-phenyl-1H-pyrazole (3a) described in the literature.