Premium
Cycloaddition reactions of ketoimines. Part II. Synthesis of substituted phenanthridines and cyclopenta[ c ]quinolines
Author(s) -
Lucchini Vittorio,
Prato Maurizio,
Scorrano Gianfranco,
Tecilla Paolo
Publication year - 1986
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.5570230435
Subject(s) - chemistry , decalin , quinoline , cycloaddition , benzene , medicinal chemistry , lewis acids and bases , sulfur , organic chemistry , catalysis
Substituted 4‐benzoyl‐3a,4,5,9b‐tetrahydro‐3 H ‐cyclopenta[ c ]quinolines 3 and 6‐benzoyl‐5,6,6a,7,8,10a‐hexahydrophenanthridines 10 are obtained through Lewis acid catalyzed addition of 1‐phenyl‐2‐arylamino‐2‐methoxyethanones 2 to cyclopentadienes and 1,3‐cyclohexadiene respectively. Compounds 3 can be converted to the aromatized analogues by reaction with 2,3‐dichloro‐5,6‐dicyanobenzoquinone in refluxing benzene. Compounds 10 are oxidized by sulfur either in decalin or in quinoline to substituted 6‐benzoylphenanthridines.