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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 para...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Maxam-Gilbert Sequencing01:05

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In the same year as the discovery of the Sanger sequencing method, another group of scientists, Allan Maxam and Walter Gilbert, demonstrated their chemical-cleavage method for DNA sequencing. The Maxam-Gilbert method relies on using different chemicals that can cleave the DNA sequence at specific sites, the separation of resulting DNA fragments of variable size using electrophoresis, and deciphering the DNA sequence from the resulting gel bands.
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Related Experiment Video

Updated: Nov 10, 2025

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
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Improved Diazo-Transfer Reaction for DNA-Encoded Chemistry and Its Potential Application for Macrocyclic

Selahattin Ede1,2, Mandy Schenk1,2, Donald Bierer3

  • 1Bayer AG, Innovation Campus Berlin, 13353 Berlin, Germany.

Molecules (Basel, Switzerland)
|April 3, 2021
PubMed
Summary

DNA-encoded libraries (DEL) enable drug discovery by converting DNA-attached amines and anilines to azides. This method facilitates the synthesis of novel macrocycles on DNA for medicinal chemistry applications.

Keywords:
DELDNA-encoded chemical librarydiazo-transfer reactionmacrocycle

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Related Experiment Videos

Last Updated: Nov 10, 2025

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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High-Density DNA and RNA microarrays - Photolithographic Synthesis, Hybridization and Preparation of Large Nucleic Acid Libraries
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High-Density DNA and RNA microarrays - Photolithographic Synthesis, Hybridization and Preparation of Large Nucleic Acid Libraries

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Molecular Biology

Background:

  • DNA-encoded libraries (DEL) are a powerful technology for identifying novel drug leads.
  • Efficient chemical transformations are crucial for expanding the utility of DEL platforms.

Purpose of the Study:

  • To develop and optimize methods for converting primary amines and anilines on DNA to azides.
  • To demonstrate the application of this methodology for synthesizing macrocycles on DNA.

Main Methods:

  • Development of diazo-transfer reactions for DNA-bound substrates.
  • Optimization of reaction conditions for high yields.
  • Proof-of-concept synthesis of macrocycles using the developed azide intermediates.

Main Results:

  • Achieved excellent yields for the conversion of primary amines and anilines to azides.
  • Demonstrated the scope and efficiency of the diazo-transfer reactions.
  • Successfully synthesized macrocycles on DNA, showcasing the method's utility.

Conclusions:

  • The developed methods provide a versatile toolkit for DEL synthesis.
  • This approach expands the chemical space accessible through DNA-encoded libraries.
  • Enables the discovery of novel macrocyclic drug candidates.