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Preparation of Amides01:29

Preparation of Amides

3.0K
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...
3.0K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.4K
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...
2.4K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
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...
2.9K
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.
3.2K
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 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.5K
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...
3.5K

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Ynamide Coupling Reagents: Origin and Advances.

Long Hu1, Junfeng Zhao1

  • 1Affiliated Cancer Hospital, Guangdong Provincial Key Laboratory of Major Obstetric Diseases, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, 511436, China.

Accounts of Chemical Research
|March 7, 2024
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Summary
This summary is machine-generated.

Ynamide coupling reagents offer a green chemistry approach to peptide synthesis, overcoming challenges like polymerization and racemization. These reagents enable efficient peptide synthesis using unprotected amino acids and are recyclable for industrial applications.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Peptide Synthesis

Background:

  • Traditional peptide synthesis relies on legacy reagents, posing challenges for sustainable development.
  • Existing methods for synthesizing peptides from unprotected amino acids suffer from polymerization or racemization.
  • There is a critical need for novel coupling reagents and strategies to address racemization in peptide synthesis.

Purpose of the Study:

  • To introduce ynamide coupling reagents as a novel solution for green peptide synthesis.
  • To demonstrate the efficacy of ynamide reagents in overcoming limitations of current peptide synthesis methods.
  • To explore the preparation, applications, and recyclability of ynamide coupling reagents.

Main Methods:

  • Development and application of ynamide coupling reagents for amide and ester bond formation.
  • Utilizing ynamide reagents for peptide fragment condensation, cyclization, and thioamide incorporation.
  • Implementing a transient protection strategy for inverse peptide synthesis with unprotected amino acids.

Main Results:

  • Ynamide coupling reagents effectively suppress racemization/epimerization, enabling practical inverse peptide synthesis.
  • Efficient ester bond formation and macrolactonization were achieved with preservation of stereochemistry.
  • A scalable, one-step synthesis for ynamide reagents was developed, along with a water-removable variant and successful recycling.

Conclusions:

  • Ynamide coupling reagents represent a significant advancement in green peptide synthesis.
  • These reagents offer a versatile and sustainable platform for various peptide-related synthetic challenges.
  • The development of ynamide coupling reagents paves the way for their broader industrial application.