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Syntheses of 6‐fluoro‐7‐piperazin‐1‐yl‐9‐cyclopropyl‐2,3,4,9‐tetrahydroisothiazolo[5,4‐ b ]quinoline‐3,4‐dione and 6‐fluoro‐7‐piperazin‐1‐yl‐9‐ p ‐fluorophenyl‐2,3,4,9‐tetrahydroisothiazolo[5,4‐ b ]quinoline‐3,4‐dione
Author(s) -
Chu Daniel T. W.
Publication year - 1990
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.5570270404
Subject(s) - chemistry , quinoline , derivative (finance) , amination , intramolecular force , stereochemistry , nucleophile , piperazine , medicinal chemistry , organic chemistry , financial economics , economics , catalysis
The syntheses of 6‐fluoro‐7‐piperazin‐1‐yl‐9‐cyclopropyl (or 9‐ p ‐fluorophenyl)‐2,3,4,9‐tetrahydroisothiazolo[5,4‐ b ]quinoline‐3,4‐diones as well as novel synthesis of isothiazolo‐3(2 H )‐one system are described. Key steps include the regiospecific displacement of a sulfinyl group and the amination of the resultant mercapto derivative followed by an intramolecular nucleophilic displacement cyclization reaction to generate the novel 2,3,4,9‐tetrahydroisothiazolo[5,4‐ b ]quinoline‐3,4‐dione nucleus.