N-Aryl-C-nitroazoles. 1. C-nitro-N-phenylazoles (Review)

Kurpet, M.; Jędrysiak, Rafał G.; Suwiński, J.

doi:10.1007/s10593-013-1205-5

Cited by 6 publications

(2 citation statements)

References 38 publications

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“…Reactions of these TACs with nitroacetylene are a potentially highly effective and selective method of synthesis of nitro-substituted, five-membered, unsaturated heterocycles that are valuable from the point of view of organic preparatory work [ 10 – 12 ]. For this reason, identification of factors determining their course is so important.…”

Section: Introductionmentioning

confidence: 99%

Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study

Jasiński

2015

Monatsh Chem

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Abstract[2 + 3] Cycloaddition reactions of nitroacetylene with allenyl-type three-atom components take place according to the polar, but a one-step mechanism. Alternatively to cycloadducts, during the reaction between the aforementioned reagents, zwitterionic structures with “extended” conformation may be formally created. However, this route is supported by neither kinetic nor thermodynamic factors.Graphical Abstract

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Section: Introductionmentioning

confidence: 99%

Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study

Jasiński

2015

Monatsh Chem

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“…This opens an opportunity to look for new N -aryl- C -nitroazoles with the desired biological activity. Very recently, we reviewed the syntheses of N -phenyl- C -nitroazoles [12], and syntheses of their derivatives will be reviewed soon. The range of methods of N -aryl- C -nitroazoles synthesis includes nitration [13], ring closure [14–15], degenerated ANRORC reactions [16], transformation of other cyclic molecules [17], oxidation of aminoazoles [18], and introduction of an aryl substituent at the ring nitrogen atom in starting nitroazole [19–20].…”

Section: Introductionmentioning

confidence: 99%

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

Kurpet

Dąbrowska²,

Jarosz³

et al. 2013

Beilstein J. Org. Chem.

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SummaryA 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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