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Related Concept Videos

Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
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...
2.0K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

5.8K
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.
5.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.3K
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...
3.3K
Nitrosation of Enols01:19

Nitrosation of Enols

2.6K
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.
2.6K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.1K
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.
4.1K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.5K
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,...
3.5K

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Updated: Jun 18, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

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

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Exploration and Development of Nitrone Chemistry.

Osamu Tamura1

  • 1Showa Pharmaceutical University.

Chemical & Pharmaceutical Bulletin
|July 31, 2024
PubMed
Summary

This review details methods for controlling nitrone reactions in organic synthesis. We present strategies for predictable and user-friendly nitrone chemistry, including nucleophilic additions and cycloadditions.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Nitrone chemistry is crucial in organic synthesis, serving as versatile 1,3-dipoles.
  • Controlling nitrone reactivity and selectivity remains a challenge in synthetic applications.

Purpose of the Study:

  • To present a comprehensive overview of strategies for enhancing the predictability and usability of nitrone reactions.
  • To categorize and discuss key advancements in controlling nitrone transformations.

Main Methods:

  • Review of synthetic methodologies involving nitrones.
  • Focus on 1,3-nucleophilic addition reactions with ketene silyl acetals.
  • Exploration of geometry-controlled and stereo-controlled cycloaddition reactions.
  • Discussion of nitrone generation via N-selective oxime modification.
Keywords:
1,3-dipolar cycloadditionE,Z-isomerizationN-selective oxime modificationcyclic nitronenitronetransesterification

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Analytical Techniques for Assaying Nitric Oxide Bioactivity
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Analytical Techniques for Assaying Nitric Oxide Bioactivity

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

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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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Analytical Techniques for Assaying Nitric Oxide Bioactivity
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Analytical Techniques for Assaying Nitric Oxide Bioactivity

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Main Results:

  • Development of predictable 1,3-nucleophilic addition reactions of ketene silyl acetals to nitrones.
  • Achieved geometry control in cycloaddition reactions of C-alkoxycarbonyl nitrones.
  • Demonstrated stereo-controlled cycloadditions through double asymmetric induction.
  • Established efficient methods for generating nitrones from oximes.

Conclusions:

  • The presented strategies significantly improve the control and predictability of nitrone reactions.
  • These advancements facilitate broader and more efficient applications of nitrones in organic synthesis.
  • Nitrone chemistry can be made more accessible and reliable through targeted synthetic development.