Ren Zhi-Lin, Lu Wen-Ting, Cai Shuang, Xiao Mi-Mi, Yuan Yue-Fei, Ding Ming-Wu
College of Chemical Engineering , Hubei University of Arts and Science , Xiangyang , Hubei Province 441053 , P.R. China.
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education , Central China Normal University , Wuhan 430079 , P.R. China.
J Org Chem. 2019 Nov 15;84(22):14911-14918. doi: 10.1021/acs.joc.9b02220. Epub 2019 Oct 28.
A one-pot novel strategy is described for the construction of various oxazolo[4,5-]quinoline derivatives starting from the isocyano(triphenylphosphoranylidene)acetates, aldehydes, amines, and 2-azidobenzoic acids. The reactions generated the target products directly in moderate to good yields via a sequential Ugi/Wittig/aza-Wittig cyclization process. The salient features of the method are that all three groups of the multifunctional isocyanides were involved in the reaction with broad substituent scopes and mild reaction conditions, making the protocol a useful contribution to the synthesis of oxazolo[4,5-]quinoline heterocycles.
描述了一种一锅法新策略,用于从异氰基(三苯基磷亚基)乙酸酯、醛、胺和2-叠氮基苯甲酸开始构建各种恶唑并[4,5 - ]喹啉衍生物。该反应通过连续的Ugi/维蒂希/氮杂维蒂希环化过程直接以中等至良好的产率生成目标产物。该方法的显著特点是多功能异氰化物的所有三组都参与了反应,具有广泛的取代基范围和温和的反应条件,这使得该方案对恶唑并[4,5 - ]喹啉杂环的合成有很大贡献。