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Ring closure reactions of methyl N ‐(haloacetyl)anthranilates with ammonia
Author(s) -
Cho Nam Sook,
Song Ki Youn,
Párkányi Cyril
Publication year - 1989
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.5570260651
Subject(s) - chemistry , yield (engineering) , ammonia , ring (chemistry) , chloroacetyl chloride , quinazoline , liquid ammonia , medicinal chemistry , closure (psychology) , organic chemistry , chloride , market economy , materials science , economics , metallurgy
In the presence of ammonia, methyl N ‐(bromoacetyl)anthranilate ( 4 ) is cyclized into 3 H ‐1,4‐benzodiaze‐pine‐2,5(1 H ,4 H )‐dione ( 1 ). However, when 4 is replaced with methyl N ‐(chloroacetyl)anthranilate ( 6 ), the only heterocyclic product formed in the reaction is 2‐(chloromethyl)quinazoline‐4(3 H )‐one ( 7 ). Under analogous conditions, 3‐haloacetamidocrotonates (9, 10) do not yield any heterocyclic products and no 1,4‐diazepines can be obtained.