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The Orientation of Oxidation of 2, 3-Diphenyl-7-hydroxyindole and Its N-Methyl Derivative with the Fremy's Salt : Studies on the Heterocyclic Quinones. I

1970; Pharmaceutical Society of Japan; Volume: 90; Issue: 10 Linguagem: Inglês

10.1248/yakushi1947.90.10_1275

1347-5231

Hisashi Ishii, Tokuo Furuse, MUTSUO KONNO, HIDEKI MITSUI, Nisaburo Ikeda,

Oxidative Organic Chemistry Reactions

Oxidation of 2, 3-diphenyl-7-hydroxyindole (VI) with Fremy's salt, [ON (SO3K)2] gave 4, 7-dihydro-2, 3-diphenylindole-4, 7-dione (X), mp 226-227°, (yield, 20%), 6, 7-dihydro-2, 3-diphenylindole-6, 7-dione (XII), mp>280°, (yield, 61%). By the same reaction, its N-methyl derivative (VII) afforded 6, 7-dihydro-2, 3-diphenyl-1-methylindole-6, 7-dione (XXI), mp 251-253°, (yield, 38.5%), as a sole product.