Synthesis of Dihydroquinolinone Derivatives via the Cascade Reaction of o-Silylaryl Triflates with Pyrazolidinones

Presented herein is a novel synthesis of dihydroquinolinone derivatives through an unprecedented cascade reaction of o-silylaryl triflates with pyrazolidinones. Mechanistically, the formation of the title products is believed to involve a cascade procedure including in situ formation of aryne and its addition with pyrazolidinone followed by N-N bond cleavage and intramolecular C-C bond formation/annulation. Compared with literature methods for the synthesis of dihydroquinolinones, this protocol has advantages such as multistep transformations accomplished in one pot, broad substrate scope, mild reaction conditions, and good tolerance of diverse functional groups. In addition, the products thus obtained demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.

Automated summary

This novel synthesis method of dihydroquinolinone derivatives involves an unprecedented cascade reaction, which includes the in-situ formation of aryne and its addition with pyrazolidinone, followed by N-N bond cleavage and intramolecular C-C bond formation. Compared to existing methods, this protocol offers advantages such as multiple transformations in one pot, a broad substrate scope, mild reaction conditions, and good tolerance of various functional groups. Additionally, the products obtained from this method demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.