A transition-metal-free one-pot sequence for the synthesis of 3-peroxy-substituted oxindoles from readily prepared 2-cyano-2-diazo-acetamides is reported. The two-step tandem process includes a highly efficient thermal intramolecular C-H-carbene insertion followed by a tetrabutylammonium iodide (TBAI) catalyzed radical C3-peroxy-functionalization. The protocol provides easy access to a new class of 3-cyano-3-peroxy-disubstituted oxindoles. Useful transformations to amides and alcohols are demonstrated.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.6b00367 | DOI Listing |
Publication Analysis
Top Keywords
3-alkylperoxy-3-cyano-oxindoles 2-cyano-2-diazo-n-phenyl-acetamides
4
2-cyano-2-diazo-n-phenyl-acetamides cyclizing
4
cyclizing carbene
4
carbene insertion
4
insertion subsequent
4
subsequent radical
4
radical oxidation
4
oxidation transition-metal-free
4
transition-metal-free one-pot
4
one-pot sequence
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!