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.
Egris
Riccardo
R
Departmento de Química Orgánica y Farmacéutica, Universidad Complutense, Facultad de Farmacia, 28040 Madrid, Spain.
Villacampa
Mercedes
M
Menéndez
J Carlos
JC
D000813:Anilides / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000813:Anilides; D007202:Indicators and Reagents; D007211:Indoles; D009574:Nitro Compounds; D015363:Quinolones; D014753:Vinyl Compounds