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
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

8.3K
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.
8.3K
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
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
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

3.2K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
3.2K

You might also read

Related Articles

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

Sort by
Same author

Clioquinol inactivates thiamine pyrophosphate by increasing cellular oxidative stress.

Redox biology·2026
Same author

Excitation Dependent Nonconventional Afterglow for 6D Dynamic Encryptions.

Advanced materials (Deerfield Beach, Fla.)·2026
Same author

Supramolecular Near-Infrared Photocatalysts for Efficient and Oxygen-Tolerant Aqueous RAFT Polymerization.

Angewandte Chemie (International ed. in English)·2026
Same author

Fluoroacetonitrile‑Based Gel Polymer Electrolytes for Fast‑Charging Lithium Metal Batteries.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2026
Same author

Soil organic carbon in arid and humid grasslands of China: Spatial heterogeneity, driving factors, and future changes.

The Science of the total environment·2026
Same author

Label-Free Fluorescence-Based Enzyme Assays Using Supramolecular Host-Guest Approaches.

Small methods·2026

Related Experiment Video

Updated: May 7, 2026

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

7.4K

Unexpected isocyanide-based cascade cycloaddition reaction with methyleneindolinone.

Jian Li1, Shikuan Su, Mengyuan Huang

  • 1Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. China. lijian@shu.edu.cn xsjia@mail.shu.edu.cn.

Chemical Communications (Cambridge, England)
|October 11, 2013
PubMed
Summary

A novel cascade reaction between isocyanide and methyleneindolinone was developed, enabling a new reaction pathway. This process efficiently opens methyleneindolinone rings and forms two new rings simultaneously.

More Related Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-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
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.1K

Related Experiment Videos

Last Updated: May 7, 2026

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

7.4K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-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
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.1K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Methyleneindolinones are versatile heterocyclic compounds.
  • Isocyanides are reactive synthons in organic synthesis.
  • Novel reaction pathways are crucial for expanding synthetic capabilities.

Purpose of the Study:

  • To establish a new cascade reaction involving isocyanide and methyleneindolinone.
  • To explore a novel reaction mode for methyleneindolinone transformation.
  • To achieve simultaneous ring-opening and ring-construction in an atom-economic manner.

Main Methods:

  • Reaction of isocyanide with methyleneindolinone under specific conditions.
  • Characterization of reaction products using spectroscopic techniques.
  • Analysis of reaction mechanism and atom economy.

Main Results:

  • An unprecedented cascade reaction was successfully established.
  • The reaction involves a novel ring-opening of methyleneindolinone.
  • Two new rings are constructed simultaneously with high atom economy.

Conclusions:

  • The developed cascade reaction offers a new synthetic strategy.
  • This transformation represents a distinct reaction mode for methyleneindolinone.
  • The method is efficient and atom-economic, valuable for organic synthesis.