Unexpected formation of (Z)-3-(halomethylene)isoindolinones from gem-dihalovinylbenzonitriles: efficient synthesis of enyne-containing isoindolinones |
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| Authors: | Chengming WangCaiyun Sun Fei WengMingchun Gao Bingxin Liu |
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| Institution: | a Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China
b Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China |
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| Abstract: | An efficient one-pot procedure for the regioselective synthesis of (Z)-3-(halomethylene)-isoindolin-1-ones was developed from easily accessible 2-(2,2-dihalovinyl)benzonitriles. From this key intermediate, a variety of isoindolinones containing an enyne moiety were synthesized in good to excellent yields via palladium-catalyzed Sonogashira reaction. The generated enyne-containing isoindolinones could be further manipulated by iodide induced cyclization reaction to afford a versatile synthetic intermediate 5H-pyrrolo2,1-a]isoindolol-5-one in high yield and could be further elaborated. |
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| Keywords: | Cross-coupling Enyne Isoindolinones Nitrogen heterocycles Palladium-catalyzed |
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