Pyridonecarboxylic acids as antibacterial gaents. VIII. An alternative synthesis of enoxacin via fluoronicotinic acid derivatives.
- 1 January 1987
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 35 (6), 2280-2285
- https://doi.org/10.1248/cpb.35.2280
Abstract
An alternative synthesis of enoxacin, a 1,8-naphthyridine antibacterial agent, was developed. The present method involves 1,8-naphthyridine ring construction by the Dieckmann type cyclization of ethyl 5-fluoronicotinate having a 2-ethoxycarbonylethylamino moiety at C-2. This nicotinate was prepared in 7 steps from ethyl fluoroacetate via ethyl 2,6-dichloro-5-fluoronicotinate.This publication has 3 references indexed in Scilit:
- Synthesis of fluorinated pyridines by the balz-schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acidJournal of Heterocyclic Chemistry, 1984
- 1,4-Dihydro-4-oxopyridinecarboxylic acids as antibacterial agents. 2. Synthesis and structure-activity relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids, including enoxacin, a new antibacterial agentJournal of Medicinal Chemistry, 1984
- Pyrimidines. 17. Novel pyrimidine to pyridine transformation reaction. One-step synthesis of pyrido[2,3-d]pyrimidinesThe Journal of Organic Chemistry, 1981