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PIFA-Mediated oxidative cyclization of 1-aroyl-N-arylcyclopropane-1-carboxamides and their application in the synthesis of pyrrolo[3,2-c]quinolinones
- Source :
- Organic Chemistry Frontiers. 4:404-408
- Publication Year :
- 2017
- Publisher :
- Royal Society of Chemistry (RSC), 2017.
-
Abstract
- An efficient ring-closing reaction was developed for the synthesis of spirocyclopropane quinolinediones from 2,2-disubstituted 2-benzoylacetamides in the presence of [bis-(trifluoroacetoxy)iodo]benzene (PIFA). This reaction proceeds at room temperature in the absence of a metal catalyst to provide spirocyclopropane quinolinediones in good to excellent yields. Furthermore, these compounds were readily converted to the corresponding pyrrolo[3,2-c]quinolinones to provide tricyclic ring structures similar to those found in the natural products martinellic acid and martinelline via an intermolecular amine ring-opening cyclization reaction.
Details
- ISSN :
- 20524129
- Volume :
- 4
- Database :
- OpenAIRE
- Journal :
- Organic Chemistry Frontiers
- Accession number :
- edsair.doi...........167540539c9376cab6c7490746e51363