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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 Amides01:29

Preparation of Amides

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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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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.6K
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...
3.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
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: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.0K
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...
4.0K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.5K
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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Asymmetric Synthesis of Functionalizable Type II β-Turn-Inducing α-Amino Acid Building Blocks.

Wenzheng Gao1, Jiaxin Han1, Sophie Greaves1

  • 1Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom.

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|August 29, 2023
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Summary

Researchers developed a new asymmetric method to create lactam-constrained amino acid building blocks. This approach preserves side chains, enabling the synthesis of potent peptidomimetics for therapeutic applications.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Peptidomimetics offer therapeutic potential but require conformational control.
  • Constrained lactams are crucial for enforcing active peptide conformations.
  • Existing methods often sacrifice side chains during lactam formation.

Purpose of the Study:

  • To develop an efficient and stereocontrolled asymmetric synthesis of lactam-constrained α-amino acid building blocks.
  • To create building blocks with diverse polar and hydrophobic side chains.
  • To demonstrate the utility of these lactams in synthesizing peptidomimetics and stabilizing β-turns.

Main Methods:

  • An novel asymmetric synthesis strategy was employed.
  • The method allows for the incorporation of various side chains.
  • The synthesized lactams were used to generate di- and tripeptides.

Main Results:

  • A new class of lactam-constrained α-amino acid building blocks was successfully synthesized.
  • The approach is versatile, accommodating a range of side chain functionalities.
  • The potential of these lactams to stabilize type II β-turns was confirmed.
  • Application in the synthesis of melanocyte-inhibiting factor peptidomimetic was demonstrated.

Conclusions:

  • The developed asymmetric method provides efficient access to valuable lactam-constrained amino acid building blocks.
  • This strategy overcomes limitations of previous methods by preserving side chains.
  • These building blocks are promising for the development of novel peptidomimetic therapeutics with enhanced stability and selectivity.