Abstract
p-Toluenesulfonyl radical can be generated by the manganese(III) acetate oxidation of sodium p-toluenesulfinate. The corresponding alkyl radicals could be produced effectively by the p-toluenesulfonyl radical induced radical reaction of allylsulfonyl substituted N-aryl amides. These alkyl radicals undergo 5-exo-trig, 6-endo-trig, or 6-exo-trig cyclization onto the aromatic ring effectively. The product distribution is highly dependent on the substituent of aromatic ring and the stability of radical intermediate. This p-toluenesulfonyl radical induced reaction provides a synthetically useful method for the synthesis of dihydroquinolinones, azaspirocyclic cyclohexadienes, and spirodihydroquinolinones.
Original language | English |
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Pages (from-to) | 3293-3301 |
Number of pages | 9 |
Journal | Tetrahedron |
Volume | 69 |
Issue number | 15 |
DOIs | |
Publication status | Published - 2013 Apr 15 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry