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Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

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.

Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

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...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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

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

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.

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...

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Updated: Jul 29, 2025

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

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

Published on: February 7, 2019

Post-Ugi Cyclizations Towards Polycyclic N-Heterocycles.

Xiao Tang¹, Liangliang Song², Erik V Van der Eycken^3,4

¹College of Science, Nanjing Forestry University, 210037, Nanjing, China.

Chemical Record (New York, N.Y.)

|May 23, 2023

Summary

This summary is machine-generated.

The Ugi reaction enables efficient synthesis of complex polycyclic N-heterocycles. Post-Ugi cyclizations, using metal catalysis or metal-free methods, create diverse structures with high step-economy.

Keywords:

Ugi gold palladium polycycle post-Ugi

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

The Ugi reaction is a versatile multicomponent reaction for synthesizing multifunctional adducts under mild conditions.
Ugi adducts can be transformed into various complex molecules, including bioactive heterocycles and natural products.
Polycyclic structures are significant in drug discovery and natural product synthesis, driving the need for efficient synthetic methods.

Purpose of the Study:

To summarize key advancements in synthesizing polycyclic N-heterocycles through post-Ugi cyclizations.
To highlight strategies developed in the Van der Eycken laboratory since 2016.
To showcase the application of transition metal catalysis and metal-free approaches in this field.

Main Methods:

Utilizing Ugi adducts as scaffolds for subsequent cyclization reactions.
Employing transition metal catalysts, including gold, rhodium, silver, and palladium.
Implementing metal-free strategies for post-Ugi transformations.

Main Results:

Successful synthesis of diverse and complex polycyclic N-heterocycles.
Demonstration of high efficiency and step-economy in the synthetic routes.
Versatility in constructing various polyheterocyclic frameworks.

Conclusions:

Post-Ugi cyclizations are powerful tools for constructing complex polycyclic N-heterocycles.
Metal-catalyzed and metal-free strategies offer efficient and versatile pathways.
This approach significantly contributes to the synthesis of valuable heterocyclic compounds.