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Chemistry
Protocolo para a Síntese de Derivados de Anilina Orto-trifluorometoxilados
Protocolo para a Síntese de Derivados de Anilina Orto-trifluorometoxilados
JoVE Journal
Chemistry
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JoVE Journal Chemistry
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocolo para a Síntese de Derivados de Anilina Orto-trifluorometoxilados

Full Text
10,916 Views
08:43 min
January 19, 2016

DOI: 10.3791/53789-v

Pengju Feng1,2, Ming-Yu Ngai1,2

1Department of Chemistry,State University of New York at Stony Brook, 2Institute of Chemical Biology and Drug Discovery,State University of New York at Stony Brook

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Please note that some of the translations on this page are AI generated. Click here for the English version.

Overview

This article presents a straightforward method for synthesizing ortho-trifluoromethoxylated aniline derivatives. The procedure involves a two-step sequence that includes O-trifluoromethylation followed by thermally induced intramolecular OCF3-migration.

Key Study Components

Area of Science

  • Organic Chemistry
  • Synthetic Methodology
  • Drug Development

Background

  • Trifluoromethoxy groups can significantly influence the properties of molecules.
  • The synthesis of novel compounds is crucial for drug discovery and agrochemical applications.
  • Existing methods may lack efficiency or scalability.
  • This study aims to address these limitations with a new synthetic approach.

Purpose of Study

  • To develop a method for synthesizing ortho-trifluoromethoxylated anilines.
  • To explore the effects of trifluoromethoxy incorporation on molecular properties.
  • To provide a scalable and efficient synthetic route for researchers.

Methods Used

  • O-trifluoromethylation of N-aryl-N-hydroxyacetamide.
  • Thermally induced intramolecular OCF3-migration.
  • Use of easy-to-handle reagents.
  • Scalable to gram-scale synthesis with broad substrate scope.

Main Results

  • Successful synthesis of ortho-trifluoromethoxylated aniline derivatives.
  • High tolerance of various functional groups.
  • Demonstrated efficiency and scalability of the method.
  • Potential applications in drug and agrochemical development.

Conclusions

  • The developed method is a valuable addition to synthetic organic chemistry.
  • It opens new avenues for the incorporation of trifluoromethoxy groups in drug design.
  • Further studies can explore the biological implications of these derivatives.

Frequently Asked Questions

What are ortho-trifluoromethoxylated anilines?
They are aniline derivatives with a trifluoromethoxy group positioned ortho to the amine, influencing their chemical properties.
Why is the trifluoromethoxy group important?
It can enhance the biological activity and stability of compounds in drug development.
What are the advantages of this synthesis method?
The method is simple, scalable, and uses readily available reagents, making it accessible for researchers.
Can this method be applied to other substrates?
Yes, the method has a broad substrate scope and can tolerate various functional groups.
What is the significance of this research?
It contributes to the development of new drugs and agrochemicals by providing a reliable synthetic route.

Um procedimento operacionalmente simples para a síntese de derivados de anilina orto-trifluorometoxilados por meio de uma sequência de duas etapas de O-trifluorometilação de N-aril-N-hidroxiacetamida seguida de migração intramolecular OCF3 induzida termicamente é relatado.

O objetivo geral deste protocolo é sintetizar novas anilinas orto-trifluorometoxiladas com a descoberta e desenvolvimento de novos medicamentos, agroquímicos e materiais funcionais. Este método pode ajudar a responder a questões-chave no campo da química estrangeira, como a incorporação do grupo trifluorometoxi em uma molécula afeta suas propriedades físicas, químicas e biológicas. A principal vantagem desta técnica é que nosso método utiliza reagentes fáceis de manusear.

É passível de ser sintetizado em escala de grama e tem amplo escopo de substrato e alta tolerância a grupos funcionais. Para a redução do 4-nitrobenzoato de metila, adicione 5,00 gramas de 4-nitrobenzoato de metila, 159 miligramas de 5% de ródio em carbono e uma barra de agitação magnética em um frasco de fundo redondo de 250 mililitros de dois gargalos seco em forno. Ligar um gargalo do balão a um colector de nitrogénio-vácuo e tapar o outro gargalo com um septo.

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Chemistry 107 Edição flúor N -aril- N -hydroxyacetamide clivagem heterolítica OCF 3 Migração Trifluoromethoxylation orto -OCF 3 Anilina

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