The Nitroethylation of Indoles. III.1-3 A Synthetic Route to Substituted Trypta mines

Wayland E Noland, Ronald F. Lange

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12 Scopus citations

Abstract

The previously described nitroethylation of indole has been extended successfully to four readily available substituted indoles: 2-methylindole, 1, 2-dimethylindole, 1-methylindole and 2-phenylindole. as had been the case with indole, the best yields of adducts were obtained with β-nitrostyrene, with good yields of adducts also often obtainable from β-methyl-β-nitrostyrene, and lesser yields from the other nitroölefins tried. Catalytic hydrogenation of the adducts yielded the corresponding tryptamines, which were converted to phthalimide derivatives. Indole-nitroölefin addition appears to be a quite general synthetic route to tryptamines from substituted indoles, as well as from indole itself.

Original languageEnglish (US)
Pages (from-to)1203-1209
Number of pages7
JournalJournal of the American Chemical Society
Volume81
Issue number5
DOIs
StatePublished - Jan 1 1959

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