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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.8K
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...
3.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.6K
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...
3.6K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.7K
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...
2.7K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.1K
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.
3.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
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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Updated: Sep 10, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Electrochemically Promoted Three-Component Synthesis for the Functionalization of N-Sulfonylformamidine.

Jia-Xiu Liu1, Xue-Yang Guo1, Shi-Jie Bo1

  • 1State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao 266042, China.

The Journal of Organic Chemistry
|August 27, 2025
PubMed
Summary

This study introduces an efficient one-pot electrochemical method to synthesize N-sulfonylformamidines from sulfonamides. The process allows for C-H functionalization and azide group introduction, demonstrating broad functional group compatibility.

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Electrochemistry

Background:

  • Sulfonamides are versatile building blocks in organic synthesis.
  • Efficient methods for functionalizing sulfonamides and introducing diverse groups are crucial for drug discovery and materials science.

Purpose of the Study:

  • To develop a novel one-pot synthetic strategy for N-sulfonylformamidines.
  • To enable direct C-H functionalization and subsequent introduction of azide groups.
  • To demonstrate the broad applicability and scalability of the developed method.

Main Methods:

  • Electrochemical synthesis of N-sulfonylformamidines from sulfonamides.
  • Shono oxidation for direct C-H bond functionalization.
  • Introduction of azide groups using imide ions and TMSN3 under Lewis acid catalysis.

Main Results:

  • A one-pot, multi-step synthetic strategy was successfully established.
  • The method demonstrated compatibility with a wide array of functional groups.
  • Successful scale-up experiments and derivatization reactions confirmed the utility of the approach.

Conclusions:

  • The developed electrochemical strategy offers an efficient and versatile route to functionalized N-sulfonylformamidines.
  • This method provides a valuable tool for accessing complex molecules with potential applications in medicinal chemistry and beyond.