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Synthesis of the cardiotonic bemarinone, 5,6‐dimethoxy‐4‐methyl‐2(1 H )‐quinazolinone, utilizing a directed metalation approach
Author(s) -
Conley Richard A.,
Barton Donald L.,
Stefanick Stephen M.,
Lam Margaret M.,
Lindabery Gregory C.,
Kasulanis Charles F.,
CescoCancian Sergio,
Currey Stephen,
Fabian Arthur C.,
Levine Seymour D.
Publication year - 1995
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.5570320312
Subject(s) - chemistry , quinazolinone , metalation , electrophile , methaqualone , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , chromatography , catalysis
Several methods for the synthesis of bemarinone, 5,6‐dimethoxy‐4‐methyl‐2(1 H )‐quinazolinone, were explored with the most successful being a directed metalation route. Details of the lithiation and the subsequent reaction with electrophiles of 3′,4′‐dimethoxy‐2,2‐dimethylpropioanilide and other derivatives of 3,4‐dimethoxyaniline are given.