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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
First domino radical cyclisation/Smiles rearrangement combination
Marc Pudlo1, Ingrid Allart-Simon, Bernard Tinant
1Institut de Chimie Moléculaire de Reims, UMR CNRS 6229, Université de Reims-Champagne-Ardenne, Faculté de Pharmacie, 51 rue Cognacq-Jay, F-51096 Reims, Cedex, France.
Chemical Communications (Cambridge, England)
|January 24, 2012
Summary
A novel domino reaction combines radical cyclization and Smiles rearrangement to create unique indolin-2-one compounds. This study details the experimental basis and reveals an unexpected tricyclic core structure.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Domino reactions offer efficient synthetic pathways.
- Smiles rearrangement is a key carbon-heteroatom bond-forming reaction.
- Indolin-2-one scaffolds are prevalent in medicinal chemistry.
Purpose of the Study:
- To develop a novel domino radical cyclisation-Smiles rearrangement.
- To synthesize 3-(2'-aryl-N-methyl acetamido)indolin-2-one derivatives.
- To investigate the reaction mechanism and explore unexpected structural motifs.
Main Methods:
- Radical cyclisation triggered by a radical initiator.
- Intramolecular Smiles rearrangement.
- Spectroscopic analysis for structural elucidation.
Main Results:
- An unprecedented domino radical cyclisation-Smiles rearrangement was achieved.
- The process successfully afforded 3-(2'-aryl-N-methyl acetamido)indolin-2-one products.
- An unexpected tricyclic core structure was discovered and characterized.
Conclusions:
- The developed domino reaction provides a facile route to complex indolin-2-one derivatives.
- The study highlights the utility of radical chemistry in complex molecule synthesis.
- The unexpected tricyclic product opens new avenues for structural exploration.
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