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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.2K
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.
4.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.6K
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.
2.6K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.4K
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.
3.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.1K
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.
12.1K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.8K
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).
2.8K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.8K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.8K

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Dioxazolone mediated cyclization reactions through C-H activation.

Ming Zhang1

  • 1College of Chemistry and Materials, Jiangxi Normal University, Nanchang 330022, China. zmchem@163.com.

Organic & Biomolecular Chemistry
|October 24, 2025
PubMed
Summary
This summary is machine-generated.

Dioxazolones are versatile reagents for synthesizing diverse heterocyclic compounds via transition-metal-catalyzed C-H activation and cyclization reactions. This method efficiently constructs various ring sizes, including macrocycles, with good functional group tolerance.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • 3-Substituted 1,4,2-dioxazol-5-ones (dioxazolones) are emerging reagents for amidation.
  • They can be converted to N-acyl nitrenes for transition-metal-catalyzed reactions.

Purpose of the Study:

  • To review dioxazolone-mediated two-component cyclization reactions via C-H activation.
  • To highlight the construction of diverse heterocyclic scaffolds using this strategy.

Main Methods:

  • Dioxazolone-directed C-H activation/cyclization with alkynes.
  • C-H amidation followed by intramolecular condensation.
  • Macrocyclization reactions.
  • Catalysis using Rh, Ru, Ir, or Co complexes.

Main Results:

  • Construction of five-membered, six-membered heterocycles, and 15- to 24-membered macrocycles.
  • Formation of various cyclization patterns ([4+1], [4+2], [5+1], [3+3], [4+n]).
  • Successful synthesis of polycyclic condensed heterocycles.
  • Good functional group compatibility, including halogens, enabling further modifications.
  • High yields (up to 99%) and rapid reaction times (down to 5 minutes at room temperature).

Conclusions:

  • Dioxazolone-mediated cyclizations offer an efficient and versatile route to complex heterocyclic structures.
  • The methodology demonstrates broad applicability in constructing diverse scaffolds and macrocycles.
  • This review serves as a reference for heterocyclic synthesis and future research.