An unexpected rearrangement of 4-alkylaminoindoles

SV Ley, RA Porter

Index: Ley, Steven V.; Porter, Roderick A. Journal of the Chemical Society, Chemical Communications, 1982 , # 23 p. 1356 - 1357

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Abstract

4-Alkylaminoindoles rearrange in good yield to the corresponding 1 -alkyl-4-aminoindoles in the presence of 10 mol% hydrated toluene-p-sulphonic acid in boiling toluene. ... During studies directed towards the total synthesis of teleocidinlA (1) (lygnbyatoxin2) and related potent tumour promotors,:3 we observed a novel and unexpected rearrange- ment of 4-alkylaminoindoles, the details of which we report here. The starting 4-alkylaminoindoles (2) used in this work ...