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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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

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

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

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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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).
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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
17.9K

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Recent Developments in Azomethine Ylide-Initiated Double Cycloadditions.

Tieli Zhou1, Xiaofeng Zhang2, Yan Jan Sheng3

  • 1College of Food Science and Engineering, Changchun University, Changchun 130022, China.

Molecules (Basel, Switzerland)
|October 16, 2025
PubMed
Summary

Azomethine ylides (AMYs) are key 1,3-dipoles for synthesizing pyrrolidine heterocycles. This study explores double cycloadditions of AMYs for novel polyheterocycles, enhancing efficiency via the PASE method.

Keywords:
amino acidazomethine ylidedecarboxylationdipolarophilesdouble cycloadditionspyrrolidine

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Azomethine ylides (AMYs) are versatile 1,3-dipoles crucial for synthesizing pyrrolidine-containing heterocycles via [3+2] cycloadditions.
  • Recent advancements focus on expanding substrate scope, improving stereoselectivity, and incorporating green chemistry principles in AMY-based cycloadditions.

Purpose of the Study:

  • To summarize double cycloaddition reactions of AMYs derived from amino esters and amino acids.
  • To present the synthesis of novel polyheterocyclic scaffolds using these reactions.
  • To discuss the application of the pot, atom, and step economic (PASE) method for enhanced reaction efficiency.

Main Methods:

  • Utilizing AMYs generated from amino esters and amino acids as 1,3-dipoles.
  • Employing [3+2] cycloaddition strategies for heterocyclic scaffold construction.
  • Applying the pot, atom, and step economic (PASE) method to optimize reaction design and efficiency.

Main Results:

  • Successful synthesis of novel polyheterocycles through double cycloadditions of AMYs.
  • Demonstration of PASE method principles for efficient and sustainable synthesis.
  • Examples provided showcase potential applications in synthesizing biologically active molecules.

Conclusions:

  • Double cycloadditions of AMYs offer a powerful route to complex polyheterocyclic structures.
  • The PASE method significantly enhances the efficiency and sustainability of these synthetic strategies.
  • The presented methodologies hold promise for the development of new biologically relevant compounds.