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Premium Ring transformations of heterocyclic compounds. XXV . Phenanthrene aldehyde imines via ring transformation of pyrylium salts with methylenedihydroisoquinolines—A novel access to the phenanthrene skeleton
Author(s)
Zimmermann Thomas,
Krautscheid Harald
Publication year2007
Publication title
journal of heterocyclic chemistry
Resource typeJournals
PublisherWiley‐Blackwell
AbstractThe ring transformation of 2,4,6‐triarylpyrylium salts 1 with 2‐methylenedihydroisoquinolines 6 , generated in situ from the related 2‐methylisoquinolinium salts 2 , in the presence of bases is reported. Whereas the transformation of 1 with 2 ( 6 ) and sodium methoxide in methanol leads to 2‐(2,4,6‐triarylphenyl)isoquinolinium salts, with sodium ethoxide in ethanol the aryl substituted phenanthrene‐9‐carbaldehyde imines 4 are obtained, the structure of which was confirmed by an X‐ray structure determination of the 1‐(4‐methylphenyl) substituted derivative. Acid catalyzed hydrolysis of the imines 4 gives rise to the parent phenanthrene aldehydes. The transformation 1 + 2 ( 6 ) → 4 represents a novel access to the phenanthrene skeleton.
Subject(s)aldehyde , biochemistry , catalysis , chemistry , ethanol , gene , medicinal chemistry , methanol , methoxide , organic chemistry , phenanthrene , ring (chemistry) , salt (chemistry) , sodium ethoxide , sodium methoxide , transformation (genetics)
Language(s)English
SCImago Journal Rank0.321
H-Index59
eISSN1943-5193
pISSN0022-152X
DOI10.1002/jhet.5570440509

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