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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

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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.
12.1K
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
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.3K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.3K
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
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.6K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.6K

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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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Modular Synthesis of Pyritide-Inspired Macrocycles Featuring Bipyridine Motifs.

Ji Hyae Lee1, Sihyeong Yi1, Juhyun Bang1

  • 1Department of Chemistry, Seoul National University, Seoul, 08826, South Korea.

Angewandte Chemie (International Ed. in English)
|October 9, 2025
PubMed
Summary

Researchers developed a novel synthesis for diverse macrocycles, leading to the discovery of 6paW, a potential ferroptosis inhibitor. This platform expands drug discovery for challenging biological targets.

Keywords:
Build/couple/pairDiversity‐oriented synthesisFerroptosis inhibitorMacrocyclePyritide

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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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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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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 α-Imino γ-Lactones and Alkylidene Pyrazolones
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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:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Macrocycles are promising scaffolds for drug development due to their unique structures.
  • They can target challenging biological interactions, including protein-protein interactions.
  • Current methods for macrocycle synthesis can be limited in scope and diversity.

Purpose of the Study:

  • To develop a diversity-oriented synthesis platform for macrocycles.
  • To construct a library of novel macrocycles inspired by pyritides.
  • To identify potential therapeutic agents, such as ferroptosis inhibitors, from the synthesized library.

Main Methods:

  • A build/couple/pair strategy was employed for macrocycle synthesis.
  • Efficient synthesis of bipyridine-based triaryl building blocks was achieved via azaindole cleavage.
  • Kinetic and cheminformatic analyses were used to assess reactivity and structural diversity.

Main Results:

  • A library of 27 diverse macrocycles was successfully constructed.
  • The synthesis platform demonstrated efficient generation of structural diversity.
  • A potential ferroptosis inhibitor, designated 6paW, was identified with clear structure-activity relationships.

Conclusions:

  • The developed synthesis platform provides a robust approach for macrocycle library design.
  • This strategy expands the accessible chemical space for drug discovery.
  • The identified ferroptosis inhibitor warrants further investigation for therapeutic potential.