Novel Synthesis of Arylfluoroquinolone Antimicrobial Agents

Abstract

A new synthetic method for preparing two arylfluoroquinolone antimicrobial agents, difloxacin and temafloxacin, was reported. 2,4- Dichloro-5-fluoroacetophenone was used as a starting material to react with diethyl oxalate in place of diethyl carbonate giving the corresponding β-keto ester in high yield. The β-keto ester was allowed to ethyloxymethenylation, amination, cyclization and hydrolysis to afford an intermediate acid with one more caxbonyl compared with that reported in the literature. After decarbonylation, it reacted with piperazine derivatives to yield the desired antibiotics. All new compounds were confirmed by 1H NMR, IR, MS spectra and elemental analysis.

Key words: difloxacin;temafloxacin;ANTIBIOTICS;AMINATION;CYCLIZATION, HYDROLYSIS;PIPERAZINE P;1HNMR;IR;MS;ELEMENTAL ANALYSIS

CLC Number:

O621

Cite this article

Dai Liyan;Chen Yingqi. Novel Synthesis of Arylfluoroquinolone Antimicrobial Agents[J]. Chin. J. Org. Chem., 2003, 23(8): 836-840.

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[1]	MA Cha, LI Long, SUN Jin-Sheng, ZHAO Feng, LI Yi-Long. Recent Progress in Dansyl-Based Dendrimers [J]. Chin. J. Org. Chem., 2011, 31(12): 1977-1988.
[2]	LIU Bin, XIE Long-Guan, XU Xiao-Hua, LI Yong-Hong. Synthesis, Crystal Structure and Herbicidal Activity of 3-Benzoyl-4-hydroxycoumarin Derivatives [J]. Chin. J. Org. Chem., 2011, 31(12): 2067-2073.
[3]	WANG Gang-Qiang, CHEN Yu-Ling, HAN Ming-Song, SUN Liang, WANG Qiu-An. Synthesis and Biological Activity of Pterostilbene and 3-Methoxy Pterostilbene and Their Glucosides Derivatives [J]. Chin. J. Org. Chem., 2011, 31(12): 2114-2120.
[4]	ZHANG Hua-Cheng, LIU Zhao-Na, XIN Fei-Fei, LI Yue-Ming, KONG Li, HAO Ai-You. Atom Transfer Radical Polymerization Based on Cyclodextrin [J]. Chin. J. Org. Chem., 2011, 31(11): 1761-1772.
[5]	ZHANG Huan, LI Hai-Gang, WU Hai-Hong. Synthesis of Chiral Imidazolinone-Based Ionic Liquids [J]. Chin. J. Org. Chem., 2011, 31(9): 1433-1439.
[6]	. Synthesis and Antitumor Activity of 5,6-2H-[1,2,4]- triazolo [3,4-b][1,3,4]thiadiazine derivatives [J]. Chin. J. Org. Chem., 2011, 31(06): 912-920.
[7]	YI Bing, ZHANG Yang, SHU Xiao-Ma, YANG Yan, DU Wen-Le, LIU Zhan-Peng. Study on Henry Reaction Catalyzed by Dendritic Amines [J]. Chin. J. Org. Chem., 2011, 31(06): 874-877.
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[9]	LIU Zhi-Chang, LIU Xiao-Xia, WANG Ying-Hong, YANG Lu. Synthesis and Biological Activities of N-Coumarin-3-formacyl-N - substitute Thioreas De-rivatives [J]. Chin. J. Org. Chem., 2011, 31(01): 136-140.
[10]	FAN Wen-Ming, GAO Jian-Rong, JIA Jian-Hong, HAN Liang, SHENG Wei-Jian, LI Yu-Jin. Solvent-Free Synthesis of β-Enamino Ketones (Esters) under High-Speed Vibration Miling (HSVM) Condition [J]. Chin. J. Org. Chem., 2010, 30(11): 1732-1736.
[11]	WANG Chao, ZHENG Xue-Fang, ZHANG Qian, LIU Qun. Progress in the Study of Different Position Substituted Thia-zolidine-4-carboxylic Acid and Its Derivatives [J]. Chin. J. Org. Chem., 2010, 30(10): 1441-1454.
[12]	XIONG Wen-Shuo, WANG Hong, YI Yu, MEI Jian-Feng, YING Guo-Qing. Progress of Crystallization-Induced Asymmetric Transformation in Resolution of Chiral Compounds [J]. Chin. J. Org. Chem., 2010, 30(07): 951-957.
[13]	YANG Xu-Hong, WU Ming-Hu, DING Ming-Wu. Synthesis of 2,2 -Disubstituted Bis(3-arylquinazolin-4(3H)-one)s [J]. Chin. J. Org. Chem., 2010, 30(07): 1032-1038.
[14]	LIU Chang-Chun, LU Wei-Ping, YAN Yan-Ning. Synthesis of Carbamates by Carbonylation of Floronitrobenzenes over TiO₂ Supported Pd-Fe Catalyst [J]. Chin. J. Org. Chem., 2010, 30(06): 843-848.
[15]	CAO Chen-Zhong, LIU Li-Qiu, CHEN Guan-Fan, ZHOU Zai-Chun, JIANG Rong-Qing, LEI Bing-Chao. Effect of Substituents on the Configuration of Stilbene Derivatives in Wittig Reaction of Substituted Benzaldehyde with Nitro-benzyltriphenylphosphonium Salt [J]. Chin. J. Org. Chem., 2010, 30(03): 395-400.

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