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Synthesis of some novel 7‐substituted quinolonecarboxylic acids via nitroso and nitrone cycloadditions
Author(s) -
Ziegler Carl B.,
Bitha Panayota,
Lin YangI
Publication year - 1988
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.5570250304
Subject(s) - nitrone , chemistry , cycloaddition , nitroso , methylene , nitroso compounds , medicinal chemistry , organic chemistry , catalysis
1‐Ethyl‐6‐fluoro‐7‐hydroxylamino‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acid 7 can be either oxidized to the corresponding nitroso intermediate 8 or converted to the methylene nitrone 9. Both intermediates form cycloaddition products with selected dienes and olefins respectively. Also, the preparation of 1‐ethyl‐6‐fluoro‐7‐(hexahydro‐2‐methyl‐5 H ‐pyrrolo[3,4‐ d ]isoxazol‐5‐yl)‐3‐quinolinecarboxylic acid 5 via a nitrone cycloaddition is presented.