Vinylation of Nitro‐Substituted Indoles,Quinolinones, and Anilides with Grignard Reagents

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.