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The synthesis of a series of 7‐amino‐1‐cyclopropyl‐8‐fluoro‐1,4‐dihydro‐4‐oxo‐1,6‐naphthyridine‐3‐carboxylic acids as potential antibacterial agents
Author(s) -
Sanchez Joseph P.,
Gogliotti Rocco D.
Publication year - 1993
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.5570300402
Subject(s) - chemistry , hexafluorophosphate , nucleophile , substituent , carboxylic acid , antibacterial activity , nitro , salt (chemistry) , amino acid , stereochemistry , medicinal chemistry , organic chemistry , bacteria , biochemistry , ionic liquid , alkyl , biology , genetics , catalysis
A series of 7‐amino‐1‐cyclopropyl‐1,4‐dihydro‐8‐fluoro‐4‐oxo‐1,6‐naphthyridine‐3‐carboxylic acids has been prepared and evaluated for antibacterial activity. These compounds were prepared by the displacement of the chloro substituent from 7‐chloro‐1‐cyclopropyl‐1,4‐dihydro‐8‐fluoro‐4‐oxo‐1,6‐naphthyridine‐3‐carboxylic acid employing the requisite nitrogen nucleophile to produce the title compounds. The naphthyridine acid was synthesized in ten steps from ethyl 2,4‐dihydroxy‐3‐nitro‐5‐pyridinecarboxylate. The key step in the sequence was a Schiemann reaction carried out using the hexafluorophosphate salt of the diazonium ion derived from ethyl 3‐amino‐2,4‐dichloro‐5‐pyridinecarboxylate.