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Nucleophilic substitution and ring closure reactions of 4‐chloro‐3‐nitro‐2‐quinolones
Author(s) -
Roschger Peter,
Fiala Werner,
Stadlbauer Wolfgang
Publication year - 1992
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.5570290141
Subject(s) - chemistry , nitration , sodium azide , nitro , nucleophilic substitution , medicinal chemistry , yield (engineering) , ring (chemistry) , nucleophile , azide , alkoxy group , substitution reaction , catalysis , nitro compound , thermal decomposition , thio , nucleophilic aromatic substitution , organic chemistry , alkyl , materials science , metallurgy
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.