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Radical-Induced Decarboxylation/Cyclization of Benzoyl Peroxides with 1,8-Enynes through In Situ SO2 Insertion/Smiles

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Summary

A new metal-free reaction forms sulfonylated indolo[2,1-a]isoquinoline derivatives using readily available materials. This efficient process enables multiple bond formations in a single radical initiation step.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Metal-free reactions are highly sought after for sustainable synthesis.
  • Multicomponent reactions offer efficiency by forming multiple bonds in one pot.
  • Indolo[2,1-a]isoquinoline derivatives are important scaffolds in medicinal chemistry.

Purpose of the Study:

  • To develop a novel metal-free multicomponent reaction.
  • To synthesize sulfonylated indolo[2,1-a]isoquinoline derivatives.
  • To utilize readily available starting materials and reagents.

Main Methods:

  • Reaction of 1,8-enynes with benzoyl peroxide and DABCO·(SO2)2.
  • A sequential in situ SO2 insertion/Smiles rearrangement/radical cyclization cascade.
  • Metal-free radical initiation.

Main Results:

  • Successful synthesis of sulfonylated indolo[2,1-a]isoquinoline derivatives.
  • High efficiency with no need for catalysts or additives.
  • Formation of one C-N, two C-C, and two C-S bonds in a single step.

Conclusions:

  • A novel, economical, and efficient metal-free multicomponent reaction has been established.
  • The developed strategy provides a facile route to valuable sulfonylated indolo[2,1-a]isoquinoline derivatives.
  • This approach offers a sustainable alternative for synthesizing complex heterocyclic compounds.