Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2-ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media.
Reactions of 2,3-indolinediones (isatins) with stabilized organometallic reagents were investigated in aqueous media. Isatins and a variety of stabilized organic halides undergo coupling under Barbier-type conditions in the presence of different metals (indium, tin, zinc) and additives (ammonium chloride, hydrobromic acid, bismuth(III) chloride, hafnium(IV) chloride). The regiochemistry of the processes (carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions) were generally excellent. On this basis, simple and fast protocols for the synthesis of the potentially bioactive 3-substituted 3-hydroxyoxindole moiety were developed.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain.
Almendros
Pedro
P
Rodríguez-Acebes
Raquel
R
D000498:Allyl Compounds / Q000138:chemical synthesis; D007202:Indicators and Reagents; D007204:Indium / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry; D015032:Zinc / Q000737:chemistry; D047090:beta-Lactams / Q000737:chemistry
D000498:Allyl Compounds; D007202:Indicators and Reagents; D007211:Indoles; D009942:Organometallic Compounds; D047090:beta-Lactams; D007204:Indium; D014001:Tin; D007510:Isatin; D015032:Zinc