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Preparation of Amides01:29

Preparation of Amides

4.2K
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...
4.2K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

7.2K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
7.2K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.8K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

4.2K
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...
4.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.8K
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...
4.8K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.7K
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...
3.7K

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Nonclassical Routes for Amide Bond Formation.

Renata Marcia de Figueiredo1, Jean-Simon Suppo1, Jean-Marc Campagne1

  • 1Institut Charles Gerhardt de Montpellier (ICGM), UMR 5253-CNRS-UM-ENSCM, Ecole Nationale Supérieure de Chimie , 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.

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Summary

This review covers modern, nonclassical methods for creating amide bonds, focusing on direct catalysis and using carboxylic acid or amine alternatives. These techniques avoid pre-activation, offering efficient synthetic strategies.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Amide bond formation is crucial in chemistry and drug discovery.
  • Traditional methods often require harsh conditions or pre-activation of reactants.
  • Nonclassical approaches offer milder and more efficient alternatives.

Purpose of the Study:

  • To provide a comprehensive overview of nonclassical amide bond formation strategies.
  • To summarize recent advancements in the field over the last two decades.
  • To categorize methods based on substrate classes and ligation strategies.

Main Methods:

  • Review of literature published within the last 20 years.
  • Classification of amide bond forming reactions based on substrate types (carboxylic acids, amines, surrogates).
  • Separate discussion of ligation strategies like Native Chemical Ligation (NCL) and Staudinger ligation.

Main Results:

  • Detailed discussion of catalytic direct amide formation from carboxylic acids and amines.
  • Exploration of amide synthesis using carboxylic acid surrogates.
  • Analysis of amide bond construction employing amine surrogates.
  • Overview of ligation strategies involving both acid and amine surrogates.

Conclusions:

  • Nonclassical methods provide powerful alternatives for amide bond construction.
  • The field has seen significant innovation in the past 20 years.
  • Diverse strategies exist, catering to various synthetic needs in organic chemistry.