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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Preparation of 1° Amines: Azide Synthesis01:22

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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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Preparation of 1° Amines: Gabriel Synthesis01:28

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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...
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Preparation of Amides01:29

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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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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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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...
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Updated: Aug 14, 2025

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Sulfamate-Tethered Aza-Wacker Cyclization Strategy for the Syntheses of 2-Amino-2-deoxyhexoses: Preparation of

Debobrata Paul1, Joel T Mague2, Shyam Sathyamoorthi1

  • 1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.

The Journal of Organic Chemistry
|January 17, 2023
PubMed
Summary

Researchers developed a novel synthesis for protected d-galactosamine using a sulfamate-tethered aza-Wacker cyclization. This new strategy offers a versatile template for creating various 2-amino-2-deoxyhexose derivatives.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • The synthesis of 2-amino-2-deoxyhexose derivatives is crucial for developing various pharmaceuticals and biologically active molecules.
  • Conventional synthetic routes often rely on glycals or hexoses as starting materials, limiting access to specific protection patterns.

Purpose of the Study:

  • To present a novel and efficient strategy for the assembly of protected d-galactosamine synthons.
  • To establish a synthetic route that allows access to 2-amino-2-deoxyhexose derivatives with challenging protection patterns.

Main Methods:

  • Utilized d-erythrono-1,4-lactone as the starting material.
  • Employed a sulfamate-tethered aza-Wacker cyclization as the key synthetic step.

Main Results:

  • Successfully assembled protected d-galactosamine synthons through a novel synthetic pathway.
  • Demonstrated the utility of the aza-Wacker cyclization in carbohydrate synthesis.
  • The developed strategy provides access to protected amino sugars not easily obtained by traditional methods.

Conclusions:

  • The presented sulfamate-tethered aza-Wacker cyclization strategy offers a new template for synthesizing diverse 2-amino-2-deoxyhexose derivatives.
  • This approach expands the synthetic toolkit for accessing complex carbohydrate structures with unique protection patterns.