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Remarkably Efficient and Direct Route to Quinolines and Benzoazepines from the Condensation of Benzoxazinediones with Phosphonium Carbanion Salts
Authors:Wafaa M Abdou  Azza A Kamel
Institution:1. Pesticide Chemistry Department , National Research Centre, Dokki , Cairo, Egypt wabdou@intouch.com;3. Pesticide Chemistry Department , National Research Centre, Dokki , Cairo, Egypt
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
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