Abstract
Abstractmagnified imageThe 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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