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The chemistry of 2 H ‐3,1‐benzoxazine‐2,4(1 H )‐dione (isatoic anhydride). 18 . A short synthesis of swietenidin A
Author(s) -
Coppola Gary M.
Publication year - 1985
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.5570220432
Subject(s) - chemistry , yield (engineering) , lithium (medication) , organic chemistry , acetic anhydride , medicinal chemistry , catalysis , medicine , materials science , metallurgy , endocrinology
N ‐Methylisatoic anhydrides react with the lithium enolate of ethyl methoxyacetate at low temperatures to produce intermediates which, when cyclized, afford 4‐hydroxy‐3‐methoxy‐2(1 H )‐quinolinones. By this route, 3‐methoxy‐ N ‐methylisatoic anhydride ( 8 ) can be converted to the alkaloid swietenidin A (2) in 71% yield.