Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

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...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

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, or cyano...

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

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

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...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

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.

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Stabilizing Lattice Oxygen Redox Through Bicarbonate Pyrolysis-Driven Multifunctional Interface Engineering in Li-Rich Layered Oxides.

Small (Weinheim an der Bergstrasse, Germany)·2026

Same author

A potent phenylalkylamine disrupts mycobacterial membrane bioenergetics and augments bactericidal activity of bedaquiline.

iScience·2025

Same author

Correction to Surface Engineering via Rare Earth Oxide Composite Coating to Enhance the High-Voltage Stability of the LiCoO<sub>2</sub> Cathode.

ACS applied materials & interfaces·2024

Same author

Surface Engineering via Rare Earth Oxide Composite Coating to Enhance the High-Voltage Stability of the LiCoO<sub>2</sub> Cathode.

ACS applied materials & interfaces·2024

Same author

Rethinking urban wilderness: Status, hotspots, and prospects of ecosystem services.

Journal of environmental management·2024

Same author

Identifying the Risk Regions of Wild Boar (<i>Sus scrofa</i>) Incidents in China.

Animals : an open access journal from MDPI·2023

Search research articles

Related Experiment Video

Updated: May 26, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

A versatile thiouronium-based solid-phase synthesis of 1,3,5-triazines.

Kah Hoe Kong¹, Chong Kiat Tan, Xijie Lin

¹Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|January 4, 2012

Summary

This summary is machine-generated.

A novel solid-phase synthesis method enables the creation of 1,3,5-triazine compounds using a thiouronium salt precursor. This versatile sulfur linker allows for diverse molecular structures, yielding 79 new compounds.

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

Related Experiment Videos

Last Updated: May 26, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

Area of Science:

Organic Chemistry
Medicinal Chemistry
Materials Science

Background:

1,3,5-triazine scaffolds are important core structures in various chemical applications.
Developing efficient and versatile synthetic routes for these scaffolds is crucial.

Purpose of the Study:

To develop a novel solid-phase synthesis for 1,3,5-triazine scaffolds.
To demonstrate the versatility of the developed method for generating diverse triazine derivatives.

Main Methods:

Utilized a solid-supported thiouronium salt as a key precursor.
Employed a stable sulfur linker for stepwise assembly of the triazine substrate.
Applied the method for synthesizing monocyclic, bicyclic, and spirocyclic compounds.

Main Results:

Successfully developed a thiouronium-based solid-phase synthesis for 1,3,5-triazines.
The sulfur linker proved stable under various reaction conditions.
A library of 79 diverse compounds featuring the 1,3,5-triazine scaffold was synthesized.

Conclusions:

The developed solid-phase synthesis offers an efficient and versatile approach to 1,3,5-triazine derivatives.
This method provides access to a wide range of complex triazine structures.
The strategy is suitable for library synthesis and drug discovery efforts.