Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

Preparation of Amides01:29

Preparation of Amides

3.4K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.4K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.2K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.9K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.7K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.7K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.4K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.4K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.2K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
3.2K

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

Visible light promotes P<sup>III</sup>/P<sup>V</sup>-catalyzed reductive <i>N</i>-arylation of nitroarenes at room temperature.

ACS catalysis·2026
Same author

Leveraging Divergent Ligand-to-Metal Charge-Transfer Excited State Pathways for Catalyst Control over Alkoxyl Radical Reactivity.

Journal of the American Chemical Society·2026
Same author

C<sub>sp</sub>, C<sub>sp</sub> <sup>2</sup>, and C<sub>sp</sub> <sup>3</sup> Hydrocarbyl Group Migration from Pd(II) to P(III): Accessing Metallophosphoranes via Nonspectator Ligand Reactivity.

Angewandte Chemie (International ed. in English)·2025
Same author

Photochemistry and Thermal Chemistry in Polymeric Ceramic Precursors.

The journal of physical chemistry letters·2025
Same author

Nitrilation of carboxylic acids by P<sup>III</sup>/P<sup>V</sup>-catalysis.

Chemical science·2025
Same author

Pyridoxal-Inspired Photo-Decarboxylase Catalysis: Photochemical Decarboxylation of Unprotected Amino Acids.

Angewandte Chemie (International ed. in English)·2025

Video Experimental Relacionado

Updated: Oct 21, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

7.5K

Síntesis y activación de amida unificadora por condensación en serie catalizada por PIII/PV: ensamblaje de tres

Jeffrey M Lipshultz1, Alexander T Radosevich1

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|September 3, 2021
PubMed
Resumen

Un nuevo método catalizado por organofosforo sintetiza eficientemente las 2-amidopiridinas a partir de aminas, ácidos carboxílicos y N-óxidos de piridina. Esta reacción en cascada automática en tándem permite la preparación modular de compuestos medicinales.

Más Videos Relacionados

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
08:55

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials

Published on: June 25, 2018

8.2K
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6.4K

Videos de Experimentos Relacionados

Last Updated: Oct 21, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

7.5K
Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
08:55

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials

Published on: June 25, 2018

8.2K
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6.4K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química medicinal

Sus antecedentes:

  • La síntesis de amida y la funcionalización generalmente requieren condiciones de reacción separadas y divergentes.
  • El desarrollo de métodos eficientes y modulares para la preparación de estructuras de amida complejas sigue siendo un desafío clave en la síntesis orgánica.

Objetivo del estudio:

  • Para reportar una nueva reacción de condensación de tres componentes catalizada por organofosforo.
  • Para lograr la síntesis de 2-amidopiridinas a través de un proceso de deshidratación en serie.
  • Demostrar la capacidad de un solo sistema catalítico para impulsar tanto la formación de amida como la funcionalidad.

Principales métodos:

  • Se utilizó un enfoque catalizado por organofosforo (PIII/PV).
  • Se utiliza una condensación de tres componentes que incluye aminas, ácidos carboxílicos y N-óxidos de piridina.
  • Incorpora un catalizador de fosfatano, un oxidante de bromo suave y un reductor de hidrosilano terminal.

Principales resultados:

  • Se generaron con éxito 2-amidopiridinas a través de una vía de deshidratación en serie.
  • Se ha logrado un control quimioselectivo tanto de la síntesis como de la funcionalidad de las amidas en una sola cascada catalítica (auto-tandem).
  • Se ha demostrado la eficacia y la modularidad del método organocatalítico desarrollado.

Conclusiones:

  • El método descrito ofrece una vía nueva y eficiente para la síntesis de 2-amidopiridina.
  • La cascada catalítica automática en tándem simplifica la preparación y la funcionalidad de la amida.
  • Este enfoque ofrece nuevas posibilidades para la síntesis modular de objetivos medicinales.