Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.4K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

29.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
29.8K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

8.2K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
8.2K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.3K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

1.7K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
1.7K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.4K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.4K

You might also read

Related Articles

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

Sort by
Same author

Gas-phase spectroscopy of H<sub>2</sub>O@C<sub>60</sub><sup>+</sup> and H<sub>2</sub>O@C<sub>60</sub>H<sup>+</sup> in the mid-infrared: the challenges of searching for endohedral fullerenes in space.

Physical chemistry chemical physics : PCCP·2026
Same author

[Assessing the risk-benefit balance of medicines: Some lessons from Covid-19].

Medecine sciences : M/S·2026
Same author

Inactivation of the Phosphatase Activity of Soluble Epoxide Hydrolase Modulates SIRT3 and Attenuates Experimental Pulmonary Hypertension.

Comprehensive Physiology·2026
Same author

Challenges in strengthening sentinel surveillance network during COVID-19 pandemic in Africa.

Scientific reports·2026
Same author

IRP1 deficiency alters mitochondrial metabolism and protects against metabolic syndrome pathologies.

JCI insight·2026
Same author

The phosphatase activity of soluble epoxide hydrolase regulates vascular calcification through the metabolism of pyrophosphate anions.

Cell death & disease·2025

Related Experiment Video

Updated: May 5, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.0K

Iron(II)-catalysed [2+2+2] cycloaddition for pyridine ring construction.

Vincent Richard1, Mélinda Ipouck, Delphine S Mérel

  • 1Normandie University, France. jean-luc.renaud@ensicaen.fr.

Chemical Communications (Cambridge, England)
|November 27, 2013
PubMed
Summary

A novel iron(II) complex serves as a simple, air-stable pre-catalyst for synthesizing substituted pyridines. This method utilizes a [2+2+2] cycloaddition reaction between diynes and nitriles.

More Related Videos

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

7.9K
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

5.0K

Related Experiment Videos

Last Updated: May 5, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.0K
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

7.9K
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

5.0K

Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Substituted pyridines are crucial heterocyclic compounds with broad applications in pharmaceuticals and materials science.
  • Efficient synthetic routes for pyridine derivatives are highly sought after in chemical research.
  • Transition metal catalysis offers powerful strategies for constructing complex organic molecules.

Purpose of the Study:

  • To develop a new, stable, and user-friendly pre-catalyst for pyridine synthesis.
  • To investigate the efficacy of an iron(II) complex in [2+2+2] cycloaddition reactions.
  • To establish a straightforward method for generating substituted pyridines from simple precursors.

Main Methods:

  • Synthesis and characterization of a novel air-stable iron(II) complex.
  • Utilizing the iron(II) complex as a pre-catalyst in a [2+2+2] cycloaddition reaction.
  • Reacting various diyne and nitrile derivatives under optimized conditions.

Main Results:

  • The iron(II) complex demonstrated high activity and stability as a pre-catalyst.
  • The [2+2+2] cycloaddition successfully yielded diverse substituted pyridine products.
  • The reaction conditions were found to be simple and amenable to air-stable operation.

Conclusions:

  • A new, simple, and air-stable iron(II) pre-catalyst enables efficient synthesis of substituted pyridines.
  • The reported [2+2+2] cycloaddition provides a valuable method for accessing pyridine derivatives.
  • This catalytic system offers a practical approach for organic chemists.