Remarkably Efficient and Direct Route to Quinolines and Benzoazepines from the Condensation of Benzoxazinediones with Phosphonium Carbanion Salts

Abstract

Treatment of 2H‐3,1‐benzoxazine‐2,4(1H)‐dione (1a) with vinyltriphenylphosphonium bromide (2a) gives substituted benzoazepine 8a (48% yield) and indolizinone 12 (27% yield), whereas substituted quinolinone 15 and benzoazepine 8b were isolated from the reaction of N‐methylisatoic anhydride (1b) and 2a. Furthermore, a series of quinoline derivatives was synthesized from the reactions of 1a and 1b with allyl‐(2b), alkyl‐(2c), (2d), and cyanomethyl‐(3) triphenylphosphonium salts.

Keywords:

• benzoazepines
• isatoic anhydrides
• phosphorus carbanions
• quinolines
• spiro compounds