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Regioselective proton‐catalyzed diarylmethylation of indoles with 9 H ‐xanthydrol, dibenzosuberenol, and bis[4‐dimethylaminophenyl]methanol
Author(s) -
Pindur Ulf,
Deschner Rainer
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250430
Subject(s) - chemistry , regioselectivity , methanol , indole test , catalysis , electrophile , medicinal chemistry , proton , stereochemistry , organic chemistry , physics , quantum mechanics
3‐Isopropylindole (4) is xanthenylated both at N‐1 (stereocontrolled major reaction), C‐2, and on the phenyl nucleus of the indole skeleton by xanthydrol (1). Other carbinols such as dibenzosuberenol (2) and bis[4‐dimethylaminophenyl]methanol (3) with lower electrophilic S N 1 activities than 1 do not react with 4 but do react very selectively with simple methylindoles to form diarylmethylated derivatives.