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Synthesis of azepinoquinazoloncs from 2‐methyl‐3‐( o ‐tolyl)‐4‐quinazolone
Author(s) -
Taylor John H.,
Harrison Derek R.,
Fried Ferdinand
Publication year - 1972
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.5570090606
Subject(s) - chemistry , sodium borohydride , methaqualone , ketone , formic acid , azepine , medicinal chemistry , organic chemistry , catalysis , chromatography
Some new azepinoquinazolones were synthesized from 2‐methyl‐3( o ‐tolyl)‐4(3 H )quinazolone (metliaqualone )as potential hypnotic agents. Methaqualone (I) reacted with dimethyl acetylene‐dicarboxylate (dmad) to give the azepinoquinazolone (II) which on treatment with PPA gave the pentacyclic ketone (V). Subsequent sodium borohydride reduction of the ketone (V) gave the fused azepine (VIa). Reaction of the azepinoquinazolone (II) with formic acid resulted in cleavage of the quinazolone nucleus to give the azepine (VIII). None of the compounds synthesized exhibited significant hypnotic activity.