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Related Concept Videos

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

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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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.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

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

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
3.9K
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...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.5K
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...
3.5K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.6K
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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Author Spotlight: Functionalizing Metal-Organic Frameworks: Advancements, Challenges, and the Power of Post-Synthetic Ligand Exchange
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A mild protocol for efficient preparation of functional molecules containing triazole.

Jing Leng1, Jie Xu1, Yanan Li1

  • 1School of Chemistry and Chemical Engineering, Yangzhou Polytechnic Institute Yangzhou Jiangsu 225127 P. R. China.

RSC Advances
|March 5, 2024
PubMed
Summary

Novel triazole molecules with sulfonyl fluoride groups were synthesized using copper-catalyzed click chemistry. These molecules can be converted to N-unsubstituted triazoles, ingeniously combining SuFEx and click chemistry.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Sulfonyl fluoride (SuFEx) click chemistry offers unique reactivity.
  • Copper-catalyzed click chemistry is a versatile tool for molecule construction.

Purpose of the Study:

  • To develop a novel synthetic strategy combining SuFEx click chemistry with Cu-catalyzed click chemistry.
  • To synthesize novel triazole molecules bearing sulfonyl fluoride functionalities.

Main Methods:

  • Cu-catalyzed click chemistry was employed for the synthesis of triazole molecules.
  • Base-mediated cleavage of sulfonyl fluoride moieties was performed.

Main Results:

  • Novel triazole molecules containing sulfonyl fluoride functionalities were synthesized in good to excellent yields.
  • Complete cleavage of sulfonyl fluoride groups under basic conditions yielded N-unsubstituted triazoles quantitatively.

Conclusions:

  • A novel and ingenious strategy for combining SuFEx click chemistry and Cu-catalyzed click chemistry was established.
  • The developed method provides efficient access to N-unsubstituted triazoles.