Metal-Free Radical-Triggered Selenosulfonation of 1,7-Enynes for the Rapid Synthesis of 3,4-Dihydroquinolin-2(1H)-ones in Batch and Flow

Jiang Kai Qiu, Cheng Shan, De Cai Wang, Ping Wei, Bo Jiang, Shu Jiang Tu, Guigen Li, Kai Guo

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21 Scopus citations

Abstract

A novel three-component selenosulfonation of 1,7-enynes with sulfinic acids and diphenyl diselenides for the formation of multifunctional 3,4-dihydroquinolin-2(1H)-ones was developed in batch and flow. This room-temperature protocol provides a highly efficient approach to diverse selenosulfones in moderate to excellent yields and with a broad scope of substrates. It should provide a potential synthesis method for the construction of diverse and meaningful 3,4-dihydroquinolin-2(1H)-ones derivatives in the fields of pharmaceutical and biological chemistry. Additionally, an obvious acceleration (20 h to 43 s) was obtained under micro flow conditions. (Figure presented.).

Original languageEnglish
Pages (from-to)4332-4339
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number24
DOIs
StatePublished - Dec 19 2017

Keywords

  • 1,7-enynes
  • 3,4-dihydroquinolin-2(1H)-ones
  • batch and flow procedures
  • metal-free process
  • selenosulfonation

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