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Some 4‐quinazolinones
Author(s) -
Mendel A.
Publication year - 1977
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.5570140131
Subject(s) - chemistry , benzoic acid , quinazolinone , benzoin , benzaldehyde , benzene , imine , organic chemistry , condensation , condensation reaction , catalysis , medicinal chemistry , physics , thermodynamics
The acid catalyzed reaction of anthranilamide with benzoin was studied under two conditions. Condensation at 150° gave known J plus unexpected quinazolinone H. In refluxing benzene (azeolropic water removal), the reactants yielded imine III. The acid catalyzed and uncatalyzed 150° reaction of III was examined by both ir and tlc. Both benzoic acid and II were formed in each case. Triethyl ortholormate with I gave quinazolinone IV while this ester with III formed II, benzaldehyde and benzoic acid.