Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid
Jun Ichi Matsumoto
1
,
Teruyuki MIYAMOTO
1
,
AKIRA MINAMIDA
1
,
Yoshiro NISHIMURA
1
,
Hiroshi Egawa
1
,
Haruki Nishimura
1
1
Research Laboratories, Dainippon Pharmaceutical Co., Ltd., Enoki 33–94, Suita, Osaka 564, Japan
|
Publication type: Journal Article
Publication date: 1984-05-01
scimago Q3
wos Q2
SJR: 0.362
CiteScore: 4.7
Impact factor: 2.4
ISSN: 0022152X, 19435193
Organic Chemistry
Abstract
Fluorination of the 2,6-disubstituted 3-aminopyridines 5 and 12 by the Balz-Schiemann reaction is described. 2,6-Dichloro-3-pyridinediazonium tetrafluoroborate (6) and 2-substituted 6-acetylamino-3-pyridinediazonium tetrafluoroborates 13 were heated with or without a solvent to give the corresponding fluorinated pyridines 7 and 14, respectively, in good yields. 2-Substituted 6-acetylamino-3-fluoropyridines (14) were converted by a known method into a series of 7-substituted 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids 21 including enoxacin [1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid [(2)], a new potential antibacterial agent.
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GOST
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Matsumoto J. I. et al. Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid // Journal of Heterocyclic Chemistry. 1984. Vol. 21. No. 3. pp. 673-679.
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Matsumoto J. I., MIYAMOTO T., MINAMIDA A., NISHIMURA Y., Egawa H., Nishimura H. Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid // Journal of Heterocyclic Chemistry. 1984. Vol. 21. No. 3. pp. 673-679.
Cite this
RIS
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TY - JOUR
DO - 10.1002/jhet.5570210309
UR - https://doi.org/10.1002/jhet.5570210309
TI - Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid
T2 - Journal of Heterocyclic Chemistry
AU - Matsumoto, Jun Ichi
AU - MIYAMOTO, Teruyuki
AU - MINAMIDA, AKIRA
AU - NISHIMURA, Yoshiro
AU - Egawa, Hiroshi
AU - Nishimura, Haruki
PY - 1984
DA - 1984/05/01
PB - Wiley
SP - 673-679
IS - 3
VL - 21
SN - 0022-152X
SN - 1943-5193
ER -
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BibTex (up to 50 authors)
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@article{1984_Matsumoto,
author = {Jun Ichi Matsumoto and Teruyuki MIYAMOTO and AKIRA MINAMIDA and Yoshiro NISHIMURA and Hiroshi Egawa and Haruki Nishimura},
title = {Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid},
journal = {Journal of Heterocyclic Chemistry},
year = {1984},
volume = {21},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/jhet.5570210309},
number = {3},
pages = {673--679},
doi = {10.1002/jhet.5570210309}
}
Cite this
MLA
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Matsumoto, Jun Ichi, et al. “Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid.” Journal of Heterocyclic Chemistry, vol. 21, no. 3, May. 1984, pp. 673-679. https://doi.org/10.1002/jhet.5570210309.