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Radical rearrangement of N-sulfonyl-N-aryl propynamides: proceeding with homolytic N–SO2 bond cleavage and 6-endo-dig cyclization toward 3-sulfonyl-2(1H)-quinolinones
- Source :
- Organic Chemistry Frontiers. 5:958-961
- Publication Year :
- 2018
- Publisher :
- Royal Society of Chemistry (RSC), 2018.
-
Abstract
- A di-tert-butyl peroxide-promoted radical rearrangement of N-sulfonyl-N-aryl propynamides has been developed. This procedure proceeds with sequential homolytic N–SO2 bond cleavage and 6-endo-dig radical cyclization to access a variety of 2-sulfonyl-3-aryl-2(1H)-quinolinones with high atom economy. The cross experiment confirmed the involvement of an intermolecular rearrangement, which was triggered by the thermo-induced homolytic cleavage of the N–SO2 bond.
- Subjects :
- Sulfonyl
chemistry.chemical_classification
010405 organic chemistry
Aryl
Organic Chemistry
Intermolecular force
010402 general chemistry
01 natural sciences
Medicinal chemistry
Radical cyclization
0104 chemical sciences
Homolysis
chemistry.chemical_compound
chemistry
Atom economy
Dig
Bond cleavage
Subjects
Details
- ISSN :
- 20524129
- Volume :
- 5
- Database :
- OpenAIRE
- Journal :
- Organic Chemistry Frontiers
- Accession number :
- edsair.doi...........0749f3eb380bc7d6a008e340ea74d063