FACILE AND CONVENIENT SYNTHESES OF FLUORINE-CONTAINING PYRIMIDO [5,4-c]QUINOLINES AND BENZO [h][1,6]NAPHTHYRIDINES BY CONDENSATION REACTION OF 2-METHOXY-3-TRIFLUOROACETYL-4-QUINOLYLAMINE WITH ALDEHYDES AND KETONES

被引:3
作者
Hatakenaka, Mizuki [1 ]
Okada, Etsuji [1 ]
机构
[1] Kobe Univ, Grad Sch Engn, Dept Chem Sci & Engn, Nada Ku, Rokkodai Cho, Kobe, Hyogo 6578501, Japan
关键词
DERIVATIVES; ANTAGONISTS; QUINOLINES; DESIGN;
D O I
10.3987/COM-16-13595
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Methoxy-3-trifluoroacetyl-4-quinolylamine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.
引用
收藏
页码:102 / 116
页数:15
相关论文
共 43 条
[1]   Synthesis, Spectroscopic Studies of Fluorinated Pyrimido-1,2,4-Triazines: Protective Effect Against Some Plant Pathogenic Fungi [J].
Aqlan, Faisal M. S. ;
Makki, Mohammed S. T. ;
Abdel-Rahman, Rada M. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (04) :1310-1317
[2]  
Bao L., PCT Int. Appl, Patent No. [WO2004093803, 2004093803]
[3]   Antileishmanial pyrazolopyridine derivatives: Synthesis and structure-activity relationship analysis [J].
de Mello, H ;
Echevarria, A ;
Bernardino, AM ;
Canto-Cavalheiro, M ;
Leon, LL .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (22) :5427-5432
[4]   SYNTHESIS AND PROPERTIES OF FLUORINE-CONTAINING HETEROCYCLIC COMPOUNDS .I. TRIFLUOROMETHYL QUINOLINES [J].
DEY, AS ;
JOULLIE, MM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1965, 2 (02) :113-&
[5]   Synthesis and Structure-Affinity Relationships of Selective High-Affinity 5-HT4 Receptor Antagonists: Application to the Design of New Potential Single Photon Emission Computed Tomography Tracers [J].
Dubost, Emmanuelle ;
Dumas, Noe ;
Fossey, Christine ;
Magnelli, Rosa ;
Butt-Gueulle, Sabrina ;
Ballandonne, Celine ;
Caignard, Daniel H. ;
Dulin, Fabienne ;
Santos, Jana Sopkova de-Oliveira ;
Millet, Philippe ;
Charnay, Yves ;
Rault, Sylvain ;
Cailly, Thomas ;
Fabis, Frederic .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (22) :9693-9707
[6]   Synthesis of some new pyrimidine derivatives and evaluation of their anticancer and antibacterial activities [J].
Fathalla, Omar A. ;
Mohamed, Neama A. ;
El-Serwy, Walaa S. ;
AbdelHamid, Hala F. ;
Abd El-Moez, Sherein I. ;
Soliman, Abdel-mohsen M. .
RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) :821-841
[7]   Design and synthesis of poly ADP-ribose polymerase-1 inhibitors.: 2.: Biological evaluation of aza-5[H]-phenanthridin-6-ones as potent, aqueous-soluble compounds for the treatment of ischemic injuries [J].
Ferraris, D ;
Ko, YS ;
Pahutski, T ;
Ficco, RP ;
Serdyuk, L ;
Alemu, C ;
Bradford, C ;
Chiou, T ;
Hoover, R ;
Huang, S ;
Lautar, S ;
Liang, S ;
Lin, QA ;
Lu, MXC ;
Mooney, M ;
Morgan, L ;
Qian, YZ ;
Tran, S ;
Williams, LR ;
Wu, QY ;
Zhang, J ;
Zou, YN ;
Kalish, V .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :3138-3151
[8]  
FILLER R, 1982, BIOMEDICAL ASPECTS F, P1
[9]  
Filler R., 1993, ORGANOFLUORINE COMPO, P1
[10]   TOPOLOGICAL PHARMACOPHORES NEW METHODS AND THEIR APPLICATION TO A SET OF ANTIMALARIALS .2. RESULTS FROM LOGANA [J].
FRANKE, R ;
STREICH, WJ .
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS, 1985, 4 (02) :51-63