Nucleophilic substitution and ring closure reactions of 4??chloro??3??nitro??2??quinolones

P Roschger, W Fiala…

Index: Roschger, Peter; Fiala, Werner; Stadlbauer, Wolfgang Journal of Heterocyclic Chemistry, 1992 , vol. 29, # 1 p. 225 - 231

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Citation Number: 63

Abstract

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 ...