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Synthesis of 3‐thiocyanato‐1 H ,3 H ‐quinoline‐2,4‐diones
Author(s) -
Klásek Antonín,
Polis Jirí,
Mrkvička Vladimír,
Košmrlj Janez
Publication year - 2002
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.5570390632
Subject(s) - quinoline , chemistry , acetic acid , nucleophile , hydrolysis , medicinal chemistry , stereochemistry , organic chemistry , catalysis
4‐Hydroxy‐1 H ‐quinolin‐2‐ones ( 1 ) react with thiocyanogen in acetic acid to the corresponding 3‐thiocyanato‐1 H ,3 H ‐quinoline‐2,4‐diones ( 2 ) in good yields. In some cases, 3‐bromo‐1 H ,3 H ‐quinoline‐2,4‐diones ( 4 ) were isolated as minor reaction products. Compounds 2 are very reactive towards nucleophiles and easily hydrolyze to the corresponding 4‐hydroxy‐1 H ‐quinoline‐2‐ones ( 1 ).