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2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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

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

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...

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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Updated: Jan 13, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Nitrones: Comprehensive Review on Synthesis and Applications.

Ricardo A L S Santos¹, Artur M S Silva¹, Diana C G A Pinto¹

¹LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3010-193 Aveiro, Portugal.

Molecules (Basel, Switzerland)

|January 10, 2026

Summary

Nitrones are versatile organic compounds crucial for synthesizing biologically active nitrogen molecules. This review details their synthesis, reactivity, and applications, emphasizing green chemistry approaches.

Keywords:

cycloaddition nitrone organic synthesis oxidation polymers spin-trap therapeutics

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Analytical Techniques for Assaying Nitric Oxide Bioactivity

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Analytical Techniques for Assaying Nitric Oxide Bioactivity

Analytical Techniques for Assaying Nitric Oxide Bioactivity

Published on: June 18, 2012

Area of Science:

Organic Chemistry
Medicinal Chemistry

Background:

Nitrones are important intermediates in organic synthesis.
They are key to creating novel nitrogen-containing biologically active compounds.

Purpose of the Study:

To provide a structured overview of nitrone synthesis and reactivity.
To highlight environmentally friendly synthetic methods.
To discuss physicochemical properties, therapeutic potential, and industrial applications.

Main Methods:

Review of synthetic methodologies for nitrones.
Analysis of nitrone transformations and reactivity.
Compilation of data on properties and applications.

Main Results:

Comprehensive summary of nitrone synthetic routes, including green approaches.
Detailed explanation of nitrone fundamental transformations and reactivity patterns.
Overview of physicochemical properties, therapeutic potential, and industrial uses.

Conclusions:

Nitrones are essential building blocks in organic synthesis.
Understanding their synthesis and reactivity is crucial for developing new drugs and materials.
Green chemistry principles are increasingly important in nitrone synthesis.