Vinylation of Nitro‐Substituted Indoles,Quinolinones, and Anilides with Grignard Reagents |
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Authors: | Riccardo Egris Mercedes Villacampa Prof J Carlos Menéndez Prof |
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Institution: | Departmento de Química Orgánica y Farmacéutica, Universidad Complutense, Facultad de Farmacia, 28040 Madrid (Spain), Fax: (+34)?91‐3941822 |
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Abstract: | The reaction of vinyl Grignard reagents with o‐methoxynitroarenes containing an electron‐releasing substituent para to the nitro group proceeds through a pathway that is different from the initially expected Bartoli indole synthesis. Thus, instead of giving fused indole derivatives, these reactions provide a very mild and efficient new procedure for the synthesis of synthetically relevant aromatic systems containing an o‐nitrovinyl moiety, such as 5‐nitro‐4‐vinylindoles, 6‐nitro‐7‐vinylindoles, 6‐nitro‐5‐vinyl‐2(1H)quinolinones, and 4‐nitro‐3‐vinylanilines. |
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Keywords: | aromatic compounds C?C coupling Grignard reaction heterocycles vinyl compounds |
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