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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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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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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).
2.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.2K
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.
10.2K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.3K
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...
8.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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.
3.6K

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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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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 functionalized pyrroloindolines through cascade radical cyclization/intermolecular

Yonggang Jiang1, Dongxiang Liu1, Lening Zhang1

  • 1Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Pharmacy, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn.

Chemical Science
|February 9, 2024
PubMed
Summary

This study introduces a novel, transition-metal-free method for synthesizing pyrroloindolines, crucial compounds in pharmaceuticals. The new approach utilizes a tandem SET/radical cyclization/intermolecular coupling reaction for efficient C3a-substituted pyrroloindoline construction.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Pyrroloindolines are vital scaffolds in natural products and pharmaceuticals.
  • Existing synthetic routes often rely on transition-metal or photoredox catalysts, limiting accessibility.
  • Developing efficient, metal-free synthetic methodologies is highly desirable.

Purpose of the Study:

  • To establish a novel, transition-metal-free synthetic route to C3a-substituted pyrroloindolines.
  • To demonstrate a tandem single-electron transfer (SET)/radical cyclization/intermolecular coupling strategy.
  • To showcase the synthetic utility and scalability of the developed method.

Main Methods:

  • A novel tandem reaction involving 2-azaallyl anions and indole acetamides.
  • Utilized single-electron transfer (SET) initiated radical cyclization followed by intermolecular coupling.
  • Employed mild and convenient reaction conditions, avoiding transition metals.

Main Results:

  • Successfully synthesized C3a-substituted pyrroloindolines without transition metals.
  • Demonstrated good functional group tolerance and yields in constructing various C3a-methylamine pyrroloindolines.
  • Achieved gram-scale sequential one-pot synthesis and hydrolysis, indicating scalability.

Conclusions:

  • The developed tandem reaction provides an efficient and metal-free pathway to valuable pyrroloindoline structures.
  • This method offers a convenient and scalable approach for pharmaceutical and chemical synthesis.
  • Highlights the potential of SET/radical cyclization cascades in complex molecule synthesis.