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

Acid Halides to Alcohols: Grignard Reaction

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...

Acid Halides to Ketones: Gilman Reagent

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...

Acid Halides to Alcohols: LiAlH4 Reduction

Acid Halides to Alcohols: LiAlH₄ Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...

Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...

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...

You might also read

Related Articles

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

Sort by

Same author

A photochemical strategy for pyrazole to imidazole conversion.

Chemical science·2026

Same author

Anticancer Potential of Piericidin A1 and Derivatives Isolated From Streptomyces sp. Associated With Palythoa variabilis From Brazilian Reefs.

Chemistry & biodiversity·2026

Same author

Repositioning HDAC Inhibitors for Glioma Treatment: Synthesis and Biological Evaluation.

ACS omega·2026

Same author

Transition-Metal-Free One-Pot Synthesis of (Hetero)chalcones with Cysteine Protease Inhibitory Activity.

ACS omega·2026

Same author

Quinazolinones as Bioisosteres of Naphthoquinones: A Path to Potent <i>Hs</i>DHODH Inhibitors with Optimized Properties.

ACS medicinal chemistry letters·2026

Same author

Salinirifamycins A-E: Rifamycin S Derivatives from the Brazilian Marine Actinomycete <i>Salinispora arenicola</i>.

Journal of natural products·2026

Search research articles

Related Experiment Video

Updated: Oct 19, 2025

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Published on: September 27, 2024

Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents.

Valter E Murie¹, Paula V Nicolino¹, Thiago Dos Santos¹

¹Departamento de Ciências BioMoleculares, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café S/N, Ribeirão Preto 14040-903, Brazil.

The Journal of Organic Chemistry

|September 23, 2021

Summary

Researchers developed functionalized quinolines using mild magnesiation of 7-chloroquinolines. Some derivatives exhibit antiproliferative properties, with a new method for optically active compounds.

More Related Videos

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Related Experiment Videos

Last Updated: Oct 19, 2025

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Published on: September 27, 2024

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Area of Science:

Organic Chemistry
Medicinal Chemistry

Background:

Quinolines are a vital scaffold in medicinal chemistry.
Developing efficient synthetic routes for functionalized quinolines is crucial.

Purpose of the Study:

To synthesize a library of functionalized quinolines.
To explore the antiproliferative potential of novel quinoline derivatives.
To develop a method for optically active quinoline synthesis.

Main Methods:

Magnesiation of 7-chloroquinolines under mild conditions.
Generation of mixed lithium-magnesium and lithium-zinc intermediates.
Reaction with various electrophiles.
Two-step synthesis for chiral derivatives.

Main Results:

Successful preparation of diverse functionalized quinolines.
Identification of 4-carbinol quinolines with antiproliferative activity.
Demonstration of a route to optically active quinolines.

Conclusions:

Mild magnesiation offers an effective route to functionalized quinolines.
Novel quinoline derivatives show promise as antiproliferative agents.
The developed methods enable access to chiral quinoline structures.