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Synthesis of an s ‐butyldibenz[ a,h ]acridine. Alkyl migration in the bernthsen reaction
Author(s) -
Klemm L. H.,
Chiang Eva,
O'Ban Gerald W.
Publication year - 1992
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.5570290249
Subject(s) - acridine , chemistry , alkyl , yield (engineering) , acridine derivatives , medicinal chemistry , organic chemistry , stereochemistry , materials science , metallurgy
The Bernthsen reaction between N ‐1‐naphthyl‐2‐naphthylamine and 2‐methylbutanoic acid and its anhydride at 200–230° for seven hours gives a low yield of 12‐ or 13‐ s ‐butyldibenz[ a,h ]acridine, instead of the expected 14‐isomer. The parent molecule dibenz[ a,h ]acridine results from the same reaction conducted at 270° for thirteen hours. It is suggested that alkyl migration may have occurred in some other cases where the Bernthsen reaction was reported to yield 14‐alkyldibenz[ a,h ]acridines.
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