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Synthesis and demethylation of new 5,6,7,8‐tetrahydro‐4,9‐dimethoxy‐1 H ‐benz[ f ]indole
Author(s) -
Malesani Giorgio,
Ferlin Maria Grazia,
Masiero Sergio
Publication year - 1982
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.5570190335
Subject(s) - chemistry , demethylation , anhydrous , indole test , yield (engineering) , aluminium chloride , benzene , medicinal chemistry , chloride , organic chemistry , stereochemistry , aluminium , biochemistry , gene expression , materials science , metallurgy , dna methylation , gene
The title compound 17 was prepared in good yield starting from 5,6,7,8‐tetrahydro‐l‐naphthol ( 9 ) by an advantageous synthesis route consisting of eight steps, as indicated in Scheme 2. Demethylation by reflux heating with anhydrous aluminium chloride in dry benzene furnished 4,9‐dihydroxy‐ and 4,9‐dioxo‐5,6,7,8‐tetrahydro‐1 H ‐benz[ f ]indoles (compounds 18 and 19 , respectively). All new products were identified on the basis of spectral and analytical data.