Ring transformations of heterocyclic compounds.  XXV  . Phenanthrene aldehyde imines via ring transformation of pyrylium salts with methylenedihydroisoquinolines—A novel access to the phenanthrene skeleton | Zendy

Zimmermann Thomas | Zendy; Krautscheid Harald | Zendy

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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 year - 2007

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.5570440509

Subject(s) - chemistry , phenanthrene , ring (chemistry) , sodium methoxide , methanol , sodium ethoxide , medicinal chemistry , aldehyde , transformation (genetics) , sodium , ethanol , aryl , organic chemistry , catalysis , biochemistry , gene , alkyl

The 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.

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