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Related Concept Videos

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

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

13.7K
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.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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.
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
5.3K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.5K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.7K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.7K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

8.4K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
8.4K

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Updated: Mar 25, 2026

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

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Dearomative cycloaddition: current trends in polycyclic indoline synthesis.

Aditi Singh1, Prashasti Kalhans1, Vikas Tyagi2

  • 1Department of Chemistry, Faculty of Science, University of Lucknow, Lucknow, 226007, Uttar Pradesh, India. chem.shashi@gmail.com.

Organic & Biomolecular Chemistry
|March 24, 2026
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Summary
This summary is machine-generated.

Dearomative cycloaddition of indoles transforms flat molecules into complex 3D structures. Recent advancements (2019-2025) highlight their use in creating polycyclic indoline frameworks with precision.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Area of Science:

  • Synthetic Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Dearomative cycloaddition is a key strategy for transforming aromatic indoles.
  • It enables the synthesis of complex, three-dimensional structures with stereochemical control.

Purpose of the Study:

  • To review recent advancements in dearomative cycloadditions of indoles (2019-2025).
  • To focus on applications in constructing polycyclic indoline frameworks with high regio- and stereoselectivity.

Main Methods:

  • Categorization of dearomative cycloadditions by reaction type: [2 + 2], [3 + 2], [4 + 2], and miscellaneous transformations.
  • Integration of synthetic applications, mechanistic insights, and future directions.

Main Results:

  • Discussion of diverse mechanistic pathways and structural outcomes for each cycloaddition type.
  • Demonstration of strategic applications in synthesizing complex polycyclic indoline frameworks.

Conclusions:

  • Dearomative cycloaddition of indoles is crucial for modern heterocyclic chemistry.
  • This strategy significantly impacts the synthesis of complex molecules.