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Eine neue Synthese von methoxylierten meso ‐Benzanthronen; Abbau zu 5,8‐Dihydroxy‐anthrachinon‐1‐carbonsäure und 5,7,8‐Trihydroxy‐anthrachinon‐1‐carbonsäure
Author(s) -
Bräm A.,
Eugster C. H.
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550324
Subject(s) - chemistry , yield (engineering) , anthracene , medicinal chemistry , carboxylate , adduct , anthraquinone , permanganate , intramolecular force , organic chemistry , metallurgy , materials science
Methyl benzoquinone carboxylate and its 5‐methoxy‐ and 6‐methoxy‐derivatives condense smoothly with β‐methoxynaphthalene in an acid catalysed reaction to give α‐arylsubstituted naphthalenes 7 , which, after reduction, methylation and intramolecular acylation yield tri‐and tetramethoxylated 7 H ‐Benz[d, e]anthracene‐7‐ones 9 . Partial degradation by means of chromic acid or permanganate leads to a regiospecific synthesis of a substituted phenalenone ( 10 ) and/or methoxy‐anthraquinone‐1‐carboxylic acids. Phthalid anion has been added on to methyl methoxy benzoquinone carboxylate to yield the adducts 4 .