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Synthesis of substituted N ‐(2,4‐dioxo‐1,2,3,4‐tetrahydroquinazolinyl)benzamides and N ‐(2‐thiono‐4‐oxo‐1,2,3,4‐tetrahydroquinazolinyl)benzamides
Author(s) -
Chau Nguyen,
Saegusa Yasuo,
Iwakura Yoshio
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.5570190318
Subject(s) - chemistry , aryl , medicinal chemistry , stereochemistry , organic chemistry , alkyl
Abstract Substituted N ‐(2,4‐Dioxo‐1,2,3,4‐tetrahydroquinazolinyl)benzamides ( 3a‐g ) and substituted N ‐(2‐Thiono‐4‐oxo‐1,2,3,4‐tetrahydroquinazolinyl)benzamides ( 4a‐g ) were synthesized in one step from the reaction of methyl anthranilate with 2‐aryl‐1,3,4‐oxadiazolin‐5‐ones ( 1a‐g ) and 2‐aryl‐1,3,4‐oxadiazoline‐5‐thiones ( 2a‐g ), respectively, in m ‐cresol at 150–160°. Alternative routes leading to the formation of 3a and 4a are also reported.