Kemp-type Elimination of 1-Arylsulfonyl-3-iodo-1h-indazoles
Synthetic communications(2021)
摘要
An intriguing ring-opening reaction of 1-arylsulfonyl-3-iodo-1H-indazoles, which can afford the corresponding ortho-(arylsulfonylamino)benzonitriles under base catalysis, was obtained unexpectedly. Herein, the optimal reaction conditions were explored and the results showed that high temperature and aprotic polar solvent are favorable to the ring-opening reaction. Most of the substrates studied can provide the corresponding ring-opening products in moderate to good yields after stirring in DMSO with K2CO3 at 120 degrees C for 18 h, suggesting the excellent compatibility of functional groups and the broad substrate scope of this reaction. Furthermore, the control experiments implied that 1-arylsulfonyl-3-iodoindazoles go through an E2 elimination mechanism similar to Kemp elimination.
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关键词
Kemp elimination,1-substituted 3-iodo-1H-indazoles,ring opening,ortho-(arylsulfonylamino)benzonitriles,E2 elimination
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