A. Da Settimo

The reactions of some indole derivatives with benzoyl nitrate. Novel oxidative coupling reactions of 2-methylindoles

Indole derivatives with a free position 3 are converted by benzoyl nitrate into the corresponding 3-nitro-derivatives. Under the same conditions, 3-methylindole gives 3-methyl-2-nitroindole, and 2,3-diphenylindole yields a mixture containing 3,3-diphenyloxindole and 6-nitro-2,3-diphenylindole. 2,3-Dimethylindole is oxidized by benzoyl nitrate to 3-methylindole-2-carbaldehyde, and under somewhat different conditions to two compounds, which, on the basis of spectral and chemical evidence, are identified as 5a,10b,12-trimethyl-5a,6,10b,11-tetrahydropyrrolo[1,2-a:5,4-b′]di-indole and the corresponding 6-nitroso-derivative. 3-Ethyl- and 3-phenyl-2-methylindole give similar products.

BROMO DERIVATIVES OF GRAMINES. PREPARATION AND PHARMACOLOGICAL PROPERTIES

Bromieten von Gramin (I) ergibt ein nicht trennbares Gemisch des 5-Bromderivates (II) mit demo-Bromderivat (III), das durch Mannich-Reaktion aus 6-Bromindol (IV) rein . erhalten wird.

A dimeric autoxidation product of 2,3-dimethylindole

A product formed in the autoxidation of 2,3-dimethylindole and in the dimerization of 2,3-dimethyl-3-hydroxy-3H-indole has been identified as 3,3a,4,8b-tetrahydro-3′,3a,8b-trimethylsopiro-[2H-furo[3,2-b]indole-2,2′-indoline]-3′-ol (V), on the basis of u.v., i.r., n.m.r., mass spectral, and chemical evidence. Several reactions of (V). involving reduction, cleavage, and rearrangements to pyrrolo[1,2-a:5,4-b′]di-indole derivatives are presented.