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Related Concept Videos

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

Acid Halides to Amides: Aminolysis

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...
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 Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.
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...

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Related Experiment Video

Updated: May 20, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

Direct α-functionalization of saturated cyclic amines.

Emily A Mitchell1, Aldo Peschiulli, Nicolas Lefevre

  • 1Organic Synthesis, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 26, 2012
PubMed
Summary

Directly functionalizing saturated cyclic amines is now possible using new synthetic methods. These approaches create reactive intermediates like cations, anions, and radicals for diverse chemical transformations.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Related Experiment Videos

Last Updated: May 20, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Direct functionalization of saturated cyclic amines remains a significant challenge in organic synthesis.
  • Developing efficient methods for modifying amine structures is crucial for drug discovery and materials science.

Purpose of the Study:

  • To review and categorize recent advancements in the direct α-functionalization of saturated cyclic amines.
  • To provide a comprehensive overview of synthetic strategies based on reactive intermediates.

Main Methods:

  • Categorization of methods based on the in situ generated reactive intermediate: α-amino cation, α-amino anion, and α-amino radical.
  • Inclusion of transition-metal-catalyzed reactions involving other intermediates as a distinct class.

Main Results:

  • Demonstration of diverse synthetic routes for α-functionalization of cyclic amines.
  • Highlighting the utility of different reactive intermediates in achieving targeted modifications.
  • Overview of novel transition-metal-catalyzed approaches.

Conclusions:

  • Significant progress has been made in the direct α-functionalization of saturated cyclic amines.
  • The described methods offer powerful tools for constructing complex amine-containing molecules.
  • Future research can build upon these strategies for broader applications in chemistry.