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Related Concept Videos

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 Nitriles01:12

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.8K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.8K
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,...
4.8K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

4.2K
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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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.9K
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...
4.9K
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...
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides.

Seiya Katahara1, Shoichiro Kobayashi1, Kanami Fujita1

  • 1Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

Journal of the American Chemical Society
|April 14, 2016
PubMed
Summary

This study introduces an iridium-catalyzed method for synthesizing functionalized nitrones from N-hydroxyamides. The novel approach offers high chemoselectivity and enables the creation of challenging cyclic and macrocyclic nitrones.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Nitrones are valuable synthetic intermediates.
  • Conventional methods for synthesizing cyclic and macrocyclic nitrones are often challenging.

Purpose of the Study:

  • To develop a novel iridium-catalyzed method for the reductive formation of functionalized nitrones from N-hydroxyamides.
  • To explore the synthesis of challenging cyclic and macrocyclic nitrones.

Main Methods:

  • Iridium-catalyzed dehydrosilylation and hydrosilylation reactions.
  • Utilized N-hydroxyamides as starting materials.
  • Employed (1)H NMR studies to investigate reaction intermediates.

Main Results:

  • Successfully synthesized functionalized nitrones with high chemoselectivity.
  • Demonstrated applicability to sensitive functional groups like methyl esters.
  • Achieved the synthesis of complex cyclic and macrocyclic nitrones.
  • Identified N-siloxyamide and N,O-acetal as key intermediates.

Conclusions:

  • The developed iridium-catalyzed method provides an efficient route to functionalized nitrones.
  • This methodology overcomes limitations of traditional synthetic approaches for nitrones.
  • The reaction proceeds via proposed N-siloxyamide and N,O-acetal intermediates.