Reactions of indoles with nitrogen monoxide: unexpected formation of azo-bis-indoles from 1,2-disubstituted indoles.
1-Methyl-, 1-ethyl-2-phenylindoles react with nitrogen monoxide, forming mainly 3,3(')-azo-bis-indoles, nitrosoindoles together with traces of nitroindoles. 2-Phenylindole, under the same experimental conditions, forms isonitrosoindole in good yields. The formation mechanism of azo-bis-indoles has been demonstrated to occur through 1,2-disubstituted nitrosoindoles by the intermediate formation of a diazonium salt.
Astolfi
Paola
P
Dipartimento di Scienze dei Materiali e della Terra, Via Brecce Bianche, Università, Ancona I-60131, Italy.
Greci
Lucedio
L
D001391:Azo Compounds / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D009569:Nitric Oxide / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis; D009603:Nitroso Compounds / Q000138:chemical synthesis
D001391:Azo Compounds; D007211:Indoles; D009574:Nitro Compounds; D009603:Nitroso Compounds; D009569:Nitric Oxide