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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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

3.5K
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.
3.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.0K
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.
10.0K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.2K
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...
8.2K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.5K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.5K

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Updated: Jun 4, 2025

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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Glycine-Based [3+2] Cycloaddition for the Synthesis of Pyrrolidine-Containing Polycyclic Compounds.

Tieli Zhou1, Xiaofeng Zhang2,3, Desheng Zhan4

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

Molecules (Basel, Switzerland)
|December 17, 2024
PubMed
Summary

This review highlights glycine as a key starting material for synthesizing biologically active pyrrolidine compounds using efficient one-pot cycloaddition and annulation reactions. It aids chemists in developing sustainable methods for novel drug discovery.

Keywords:
Glycineannulationazomethine ylidescycloadditiondipolarophilepyrrolidine

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

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Heterocyclic Chemistry

Background:

  • Pyrrolidine derivatives are crucial scaffolds in medicinal chemistry, exhibiting diverse biological activities.
  • Developing efficient synthetic routes to these compounds is an ongoing challenge in organic synthesis.
  • Glycine offers a readily available and versatile chiral pool starting material for constructing pyrrolidine rings.

Purpose of the Study:

  • To review recent advancements in glycine-based [3+2] cycloaddition reactions for pyrrolidine synthesis.
  • To explore the integration of other annulation strategies in one-pot procedures.
  • To provide insights into synthetic methodology, scope, mechanisms, and potential applications in drug discovery.

Main Methods:

  • Literature review focusing on glycine-derived [3+2] cycloadditions.
  • Analysis of one-pot multi-component reactions for pyrrolidine assembly.
  • Discussion of reaction mechanisms and substrate scope variations.

Main Results:

  • Compilation of various glycine-based strategies for constructing pyrrolidine heterocycles.
  • Demonstration of the efficiency of one-pot approaches for complex molecule synthesis.
  • Overview of the substrate scope and mechanistic pathways involved.

Conclusions:

  • Glycine is a valuable precursor for synthesizing diverse pyrrolidine compounds.
  • One-pot cycloaddition and annulation reactions offer efficient and sustainable routes.
  • The reviewed methods facilitate the preparation of potential drug candidates.