Synthetic Communications p. 1249 - 1256 (2016)
Update date:2022-08-03
Topics:
Sun, Guofeng
Cheng, Fengkai
Tao, Ruiheng
Sun, Yuxing
Pan, Jinpeng
Zhu, Yaohua
Wang, Zhonghua
Wu, Fanhong
Yin, Yan
A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer–Schuster rearrangement/intramolecular hydroamination reaction process.
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