Nucleophilic substitution and ring closure reactions of 4‐chloro‐3‐nitro‐2‐quinolones
- 1 January 1992
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 29 (1) , 225-231
- https://doi.org/10.1002/jhet.5570290141
Abstract
4‐Chloro‐3‐nitro‐2‐quinolones 3 obtained from the 4‐hydroxy quinolones 1 by nitration and chlorination, reacted with sodium azide to the 4‐azido derivatives 4 which cyclized on thermolysis to yield the furoxanes 5. Nucleophilic substitution reactions of 3 led to the 4‐amino‐, 4‐fluoro‐ and 4‐alkoxy‐3‐nitroquinolones 7, 8 and 9, respectively. With thiols either 4‐thio‐3‐nitro‐ 10 or 3,4‐dithioquinolones 11 were obtained depending on the basic catalyst.Keywords
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