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Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

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The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.
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Diels–Alder Reaction: Characteristics of Dienes01:29

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
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Diels–Alder Reaction: Characteristics of Dienophiles01:24

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In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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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.
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The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
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A Five-Component Biginelli-Diels-Alder Cascade Reaction.

Taber S Maskrey1, Madeline C Frischling1, Mikhaila L Rice1

  • 1Department of Chemistry, University of Pittsburgh, Pittsburgh, PA, United States.

Frontiers in Chemistry
|September 14, 2018
PubMed
Summary
This summary is machine-generated.

A novel five-component condensation reaction was discovered, synthesizing complex dihydropyrimidinone products. This reaction proceeds via a Biginelli intermediate and a formal hetero Diels-Alder cycloaddition, offering a new synthetic pathway.

Keywords:
5-CCBiginelli reactionInBr3dihydropyrimidinonehetero Diels-Alder reactionmulti-component condensation

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Multi-component reactions (MCRs) are efficient synthetic tools.
  • Biginelli reactions produce dihydropyrimidinones, valuable heterocyclic compounds.

Purpose of the Study:

  • To discover a new multi-component condensation reaction.
  • To synthesize a novel five-component condensation product.

Main Methods:

  • Reaction of urea, beta-keto ester, and formaldehyde with catalytic indium bromide.
  • Characterization of the product using Nuclear Magnetic Resonance (NMR) and Nuclear Overhauser Effect (NOE) analysis.
  • Mechanistic studies involving a Biginelli intermediate.

Main Results:

  • Discovery of a new five-component condensation reaction.
  • Synthesis of a complex dihydropyrimidinone derivative.
  • Confirmation of product structure and proposed stepwise mechanism via experimental evidence.

Conclusions:

  • A novel five-component condensation reaction has been developed.
  • The reaction proceeds through a Biginelli intermediate and a formal hetero Diels-Alder reaction.
  • This work expands the synthetic utility of MCRs and dihydropyrimidinone synthesis.