Eine neue Synthese von methoxylierten  meso ‐Benzanthronen; Abbau zu 5,8‐Dihydroxy‐anthrachinon‐1‐carbonsäure und 5,7,8‐Trihydroxy‐anthrachinon‐1‐carbonsäure | Zendy

Bräm A. | Zendy; Eugster C. H. | Zendy

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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 .

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