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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.7K
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...
2.7K
Preparation of Amides01:29

Preparation of Amides

3.2K
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...
3.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
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...
4.1K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.1K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
3.1K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
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.
3.3K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.5K
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...
3.5K

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Updated: Aug 28, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Challenges and Breakthroughs in Selective Amide Activation.

Minghao Feng1, Haoqi Zhang1,2, Nuno Maulide1,2

  • 1Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.

Angewandte Chemie (International Ed. in English)
|September 20, 2022
PubMed
Summary
This summary is machine-generated.

Amides, typically unreactive carbonyl compounds, are now being selectively activated under mild conditions. Recent advancements reveal novel strategies, marking a new era in amide activation chemistry.

Keywords:
Amide ActivationAmide FunctionalisationElectrophilic ActivationSynthetic MethodsTransition-Metal Catalysis

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Amides are traditionally considered less reactive than ketones and esters due to their electronic and structural properties.
  • Recent research has focused on developing methods for the selective activation of amides under mild conditions.

Purpose of the Study:

  • To review recent advances in selective amide activation strategies.
  • To highlight new trends and breakthroughs in the field of amide chemistry.

Main Methods:

  • Review of novel activation strategies for amides.
  • Analysis of synthetically useful and mechanistically intriguing transformations.

Main Results:

  • Several new methods have been developed for selective amide activation.
  • These methods enable a range of useful chemical transformations.

Conclusions:

  • The field of amide activation is rapidly developing.
  • Recent breakthroughs indicate a "new age" for amide activation, offering exciting possibilities for synthetic chemistry.