Reação de Henry com nitrosoarenos
Nitrogen functional groups are common structural fragments in biologically active natural or synthetic molecules. Nitroso compounds have proved to be valuable substrates to synthesize these molecules by means of a wide range of transformations in which they can be employed either as electrophiles or...
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| Formato: | bachelorThesis |
| Idioma: | pt_BR |
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Universidade Federal do Rio Grande do Norte
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| Endereço do item: | https://repositorio.ufrn.br/handle/123456789/38270 |
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| Resumo: | Nitrogen functional groups are common structural fragments in biologically active natural or synthetic molecules. Nitroso compounds have proved to be valuable substrates to synthesize these molecules by means of a wide range of transformations in which they can be employed either as electrophiles or hetero-dienophiles. Remarkably, the addition of enolates to nitroso compounds gives access to C-N and C-O bonds through modular protocols. This type of reaction demonstrates the resemblance between the reactivity of nitroso compounds and aldehydes along with the versatility of nitroso electrophiles. In this scenario, this work aimed to employ nitrosoarenes as aldehydes analogue in Henry-type reactions in order to obtain the N-selective addition product whose structure incorporates two different nitrogen functional groups and characterizes unprecedented moieties. To accomplish this, the reaction between nitromethane and nitrosobenzene was studied using either a one-pot designed approach or a strategy that involved the in situ formation of the nitroso partner from oxidation of aniline. The reaction media GC/MS analyses for both reaction designs were able to detect only the aniline oxidation byproducts. Unexpectedly, neither the targeted product nor nitroso starting material could be identified in the chromatograms. These results point out the need to improve the method to product detection in order to prove the concept of the suggested chemistry. |
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