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The chemistry of 2 H ‐3,1‐benzoxazine‐2,4(1 H )‐dione (isatoic anhydride). 9 . Synthesis of 2‐arylquinoline alkaloids
Author(s) -
Coppola Gary M.
Publication year - 1982
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.5570190405
Subject(s) - chemistry , acetophenone , yield (engineering) , lithium (medication) , organic chemistry , medicinal chemistry , aryl , catalysis , alkyl , metallurgy , endocrinology , medicine , materials science
A one‐step synthesis of N ‐methyl‐2‐aryl‐4‐quinolone alkaloids is described. These compounds are readily prepared from the reaction of an N ‐methylisatoic anhydride with the lithium enolate of an acetophenone. By this method, the reaction of N ‐methylisatoic anhydride ( 5 ) or 5‐methoxy‐ N ‐methylisatoic anhydride ( 7 ) with acetophenone produces the alkaloids N ‐methyl‐2‐phenyl‐4‐quinolone ( 1 ) and eduline ( 2 ) in 81% and 70% yield, respectively. An analogous reaction of 5 with 3,4‐methylenedioxyacetophenone gives graveoline ( 3 ) in 63% yield whereas 7 and α‐methoxyacetophenone affords japonine ( 4 ) in 61% yield.