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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.2K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.1K
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...
3.1K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.4K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.4K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
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.
3.3K

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Author Spotlight: Functionalizing Metal-Organic Frameworks: Advancements, Challenges, and the Power of Post-Synthetic Ligand Exchange
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Functionalized Triazines and Tetrazines: Synthesis and Applications.

Joydip Mondal1, Akella Sivaramakrishna2

  • 1Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology (VIT), Vellore, Tamil Nadu, 632 014, India.

Topics in Current Chemistry (Cham)
|June 23, 2022
PubMed
Summary

Triazine and tetrazine molecules are versatile heterocyclic compounds with diverse biological activities. This review details their synthesis, properties, and applications in medicine and chemical biology.

Keywords:
ApplicationsReactivitySynthesisTetrazinesTriazines

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Chemical Biology

Background:

  • Triazine and tetrazine compounds are heterocyclic molecules with significant biological importance.
  • Their derivatives exhibit a wide range of pharmacological activities, including antifungal, anticancer, and antiviral properties.

Purpose of the Study:

  • To review recent advancements in the synthesis and coordination properties of triazine and tetrazine molecules.
  • To explore the diverse applications of these heterocyclic systems in various scientific fields.

Main Methods:

  • Microwave-assisted synthesis
  • Solid-phase synthesis
  • Metal-based reactions
  • [4+2] cycloaddition reactions
  • Multicomponent one-pot reactions

Main Results:

  • Various synthetic routes for triazine and tetrazine derivatives have been developed.
  • These molecules undergo diverse organic transformations, enabling the creation of complex structures.
  • Bioorthogonal applications in chemical biology have emerged as a promising area.

Conclusions:

  • Triazine and tetrazine chemistry offers a rich platform for designing novel biologically active molecules.
  • Further research into their synthesis and applications holds significant potential for drug discovery and chemical biology.