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Related Concept Videos

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

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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.
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Amides to Amines: LiAlH4 Reduction01:20

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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.4K
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...
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Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
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Convenient Entry to 18F-Labeled Amines through the Staudinger Reduction.

E Johanna L Stéen1,2, Vladimir Shalgunov1, Christoph Denk3

  • 1Department of Drug Design and Pharmacology University of Copenhagen Universitetsparken 2 DK-2100 Copenhagen Denmark.

European Journal of Organic Chemistry
|April 23, 2019
PubMed
Summary

This study introduces a new method for synthesizing positron emission tomography (PET) tracers by converting fluorine-18 labeled azides to amines using Staudinger reduction, enhancing tracer development.

Keywords:
AminesAzidesFluorineRadiochemistryReduction

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Area of Science:

  • Radiochemistry
  • Organic Synthesis
  • Medical Imaging

Background:

  • Fluorine-18 is ideal for positron emission tomography (PET) imaging due to its decay properties.
  • Developing efficient methods to incorporate fluorine-18 into bioactive molecules is crucial for advancing PET tracer development.
  • Indirect 18F-labeling using amino-functionalized synthons offers a versatile route to various PET tracers.

Purpose of the Study:

  • To report a novel method for converting 18F-labeled azides to primary amines.
  • To demonstrate the utility of the Staudinger reduction for 18F-labeling applications.
  • To enhance the flexibility and efficiency of synthesizing diverse 18F-labeled PET tracers.

Main Methods:

  • Conversion of 18F-labeled azides (aliphatic and aromatic) to primary amines.
  • Utilizing the Staudinger reduction for the azide-to-amine transformation.
  • Automation of the developed synthetic method.

Main Results:

  • High conversion yields were achieved for both aliphatic and aromatic 18F-labeled azides to amines.
  • The Staudinger reduction method proved effective for 18F-labeled azide conversion.
  • The method was successfully automated, simplifying the synthesis process.

Conclusions:

  • The Staudinger reduction provides an efficient route to synthesize 18F-labeled primary amines from azides.
  • This strategy generates two valuable synthons from a single precursor, increasing synthetic flexibility.
  • The method facilitates the labeling of diverse chemical scaffolds with minimal synthetic effort, advancing PET tracer development.