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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

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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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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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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.4K
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...
8.4K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
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.
2.1K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.1K
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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Instant Macrocyclizations via Multicomponent Reactions.

Michael Fragkiadakis1, Paraskevi-Kleio Anastasiou1, Marios Zingiridis1

  • 1Department of Chemistry, University of Crete, Voutes, 70013 Heraklion, Greece.

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Chemists can now rapidly synthesize challenging medium-sized macrocycles using a novel, sustainable two-step method. This efficient approach utilizes orthogonal multicomponent reactions (MCRs) for straightforward access to valuable macrocyclic compounds.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Macrocycles are crucial structural motifs with diverse applications.
  • Existing synthetic methods for macrocycles often lack efficiency and sustainability.
  • Accessing medium-sized macrocycles remains a synthetic challenge.

Purpose of the Study:

  • To introduce a rapid and sustainable method for macrocycle synthesis.
  • To provide straightforward access to medium-sized macrocycles.
  • To explore orthogonal multicomponent reaction (MCR) strategies.

Main Methods:

  • A two-step, one-pot synthesis was developed.
  • The protocol employs orthogonal Ugi and Groebke-Blackburn-Bienaymé multicomponent reactions (MCRs).
  • Isocyanides tethered to alkyl tosylates were utilized as key building blocks.

Main Results:

  • The method efficiently yields medium-sized macrocycles.
  • Single crystal X-ray structures revealed conformational reorganization driven by intramolecular hydrogen bonding.
  • Computational modeling provided insights into the synthesized macrocyclic libraries.

Conclusions:

  • The developed MCR-based protocol offers an efficient and sustainable route to medium-sized macrocycles.
  • This approach overcomes limitations of previous synthetic strategies.
  • The study provides a valuable new tool for macrocyclic chemistry and drug discovery.