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Related Concept Videos

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...
2.5K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.9K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
4.9K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

5.8K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
5.8K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.3K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
10.3K
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

3.5K
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Related Experiment Video

Updated: Jul 31, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

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Site-Selective Amide Functionalization by Catalytic Azoline Engrafting.

Wyatt C Powell1, Garrett E Evenson1, Maciej A Walczak1

  • 1Department of Chemistry, University of Colorado, Boulder, Colorado 80309, United States.

ACS Catalysis
|May 4, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel artificial cyclodehydratase for selective peptide and natural product modification. This catalyst efficiently grafts heterocycles onto amide groups, offering a sustainable alternative to existing methods.

Keywords:
azoleazolinemolybdenumpeptidessite-selective functionalization

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Biochemistry

Background:

  • Direct activation of peptide and protein amide groups is difficult due to their inherent stability.
  • While enzymes offer high selectivity, small-molecule catalysts for amide functionalization are limited.
  • Existing methods often lack the broad substrate scope and efficiency required for complex molecules.

Purpose of the Study:

  • To design a novel catalytic system for site-selective modification of peptides and natural products.
  • To develop a small-molecule catalyst that mimics enzymatic selectivity for amide bond functionalization.
  • To create a sustainable and efficient method for introducing heterocycles into biomolecules.

Main Methods:

  • Designed an artificial cyclodehydratase featuring a molybdenum(VI) center coordinated by a sterically hindered tripod ligand.
  • Employed the catalyst for site-selective introduction of azolines into various small molecules, natural products, and oligopeptides.
  • Demonstrated functionalization of a single amide group among multiple similar positions and subsequent conversion to amines and thioamides.

Main Results:

  • The optimized catalyst efficiently introduced azolines into diverse substrates with minimal waste.
  • Achieved high selectivity in functionalizing a single amide bond even in the presence of up to seven similar sites.
  • Successfully converted amide groups into amines and thioamides, showcasing the catalyst's versatility.

Conclusions:

  • The developed artificial cyclodehydratase provides a new mechanistic paradigm for peptide and natural product functionalization.
  • This catalytic system addresses the need for a general, selective, and sustainable method for modifying amide bonds.
  • The approach offers broad applicability in synthetic chemistry and drug discovery.