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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

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...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...

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Ynamides: versatile tools in organic synthesis.

Gwilherm Evano1, Alexis Coste, Kévin Jouvin

  • 1Institut Lavoisier de Versailles, UMR CNRS, Université de Versailles Saint-Quentin en Yvelines, France. evano@chimie.uvsq.fr

Angewandte Chemie (International Ed. in English)
|April 1, 2010
PubMed
Summary

Ynamides, versatile organic synthesis building blocks, offer unique nitrogen incorporation. Recent advances have spurred new reactions and synthetic applications for these valuable nitrogen-substituted alkynes.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Ynamides possess a unique balance of stability and reactivity.
  • They enable the incorporation of nitrogen functionalities into organic molecules.
  • Ynamides are increasingly recognized as versatile building blocks in organic synthesis.

Purpose of the Study:

  • To review recent breakthroughs in ynamide synthesis and applications.
  • To highlight the growing importance of nitrogen-substituted alkynes in modern chemistry.
  • To showcase novel reactions and synthetic strategies involving ynamides.

Main Methods:

  • Literature review of recent publications on ynamides.
  • Analysis of synthetic methodologies and reaction development.
  • Compilation of key examples demonstrating ynamide utility.

Main Results:

  • Significant advancements in ynamide preparation techniques.
  • Discovery of numerous new reactions utilizing ynamides.
  • Expansion of synthetic sequences incorporating ynamides for complex molecule synthesis.

Conclusions:

  • Ynamides are crucial intermediates in contemporary organic synthesis.
  • Continued research is yielding innovative applications for these compounds.
  • The field of ynamide chemistry is rapidly expanding with new discoveries.