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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
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.
3.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.5K
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...
4.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

4.6K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.6K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

5.8K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
5.8K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.5K
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...
3.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.8K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.8K

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Rubazonic Acids and Their Synthesis.

My Linh Tong1, Lena Theresa Leusch1, Kristina Holzschneider1

  • 1Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany.

The Journal of Organic Chemistry
|April 16, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed a simple one-pot synthesis for rubazonic acid dyes from pyrazolones. This practical method avoids hazardous intermediates, offering broad access to diverse rubazonic acid derivatives.

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Area of Science:

  • Organic Chemistry
  • Dye Synthesis
  • Heterocyclic Chemistry

Background:

  • Rubazonic acids are a known class of dyes with limited documented syntheses and applications.
  • Existing synthetic routes may involve hazardous intermediates or lack practicality.
  • There is a need for efficient and accessible methods for rubazonic acid preparation.

Purpose of the Study:

  • To establish a straightforward and practical one-pot synthesis for rubazonic acid derivatives.
  • To develop alternative methods for synthesizing more complex rubazonic acid variants.
  • To provide a safer and more accessible route to these valuable compounds.

Main Methods:

  • A one-pot oxidative diazidation followed by reductive work-up of 1H-pyrazol-5(4H)-ones.
  • An alternative two-step procedure involving controlled hydrogenation for challenging derivatives.
  • Characterization of synthesized rubazonic acid compounds.

Main Results:

  • Successful synthesis of a broad range of rubazonic acid derivatives using the one-pot method.
  • Avoidance of isolation of potentially hazardous diazido intermediates.
  • Efficient preparation of complex rubazonic acid variants through the two-step procedure.

Conclusions:

  • The developed one-pot protocol offers a simple, practical, and safe route to diverse rubazonic acids.
  • The alternative two-step method provides access to challenging rubazonic acid structures.
  • This work expands the synthetic accessibility and potential applications of rubazonic acid dyes.