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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...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...
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...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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.

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Related Experiment Video

Updated: Jun 16, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Modular Maleimide Synthesis from Ynamides.

Thibault Heymans1, Loïc Durand-Baudet1, Yohann Landrain1

  • 1Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.

Organic Letters
|June 15, 2026
PubMed
Summary

Researchers developed an efficient strategy to synthesize functional maleimides from ynamides and α-ketoesters. This cascade reaction provides rapid access to diverse maleimide scaffolds and related heterocycles.

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

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Last Updated: Jun 16, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Maleimides are crucial heterocyclic compounds with diverse applications in medicinal chemistry and materials science.
  • Efficient synthetic routes to functionalized maleimides are highly sought after.

Purpose of the Study:

  • To develop a general and efficient strategy for synthesizing densely functionalized maleimides.
  • To explore the diversification of maleimide scaffolds into other heterocyclic systems.

Main Methods:

  • A cascade sequence involving ynamides and α-ketoesters via in situ generated lithiated ketenimines.
  • The sequence includes formal anionic (2 + 2) cycloaddition, cycloreversion, and cyclocondensation.
  • Conditions allow for retention or removal of the N-protecting group.

Main Results:

  • Rapid access to a wide range of densely functionalized maleimides with excellent functional group tolerance.
  • Demonstrated diversification of maleimide scaffolds into distinct heterocycles using a "nitrogen switch" strategy.
  • Successful concise syntheses of denigrin A, aqabamycin A, and a unified synthesis of antrodins A-C.

Conclusions:

  • The reported method is a versatile platform for the rapid construction of functional maleimide architectures.
  • This strategy offers efficient access to complex molecules and facilitates further chemical exploration.