3-nitroquinoline derivatives as well as preparation method and application thereof
A technology for nitroquinolines and derivatives, which is applied in the directions of drug combination, organic chemistry, antitumor drugs, etc., can solve the problems of low synthesis yield, high temperature, long reaction time, etc., and achieves short synthesis route and low production cost. , the effect of easy operation
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Embodiment 1
[0068] Example 1: Synthesis of 6-fluoro-3-nitro-N-(4-(trifluoromethyl)benzyl)-2-(4-(trifluoromethyl)benzylamino)quinoline-4-methyl Amide (Compound 1)
[0069] In a 25 mL round bottom flask add 2-nitro-N,N'-bis(4-(trifluoromethyl)benzyl)ethylene-1,1-diamine (1 mmol) and 5-fluorodihydro After indole-2,3-dione (1.1 mmol), add toluene (15 ml) and acetic acid (4 mmol) and heat to reflux under magnetic stirring, and react under reflux for 16 hours. TLC monitors the reaction, and after the raw material point disappears completely, 50 milliliters of ethyl acetate and 50 milliliters of saturated aqueous sodium chloride are added to the reaction solution for extraction, and the organic layer is washed with anhydrous NaCl. 2 SO 4 For drying, the dried organic phase was concentrated to dryness under reduced pressure, and then 3 ml of acetone and 4 grams of 100-200 mesh silica gel were added to the concentrated and evaporated product, stirred evenly, evaporated to dryness under reduced p...
Embodiment 2
[0073] Example 2: Synthesis of 6-fluoro-N-(4-fluorobenzyl)-2-(4-fluorobenzylamino)-3-nitroquinoline-4-formamide (compound 2)
[0074] Add N,N'-bis(4-fluorobenzyl)-2-nitroethylene-1,1-diamine (1 mmol) and 5-fluoroindoline-2 to a 25 mL round bottom flask, After adding 3-diketone (1.1 mmol), toluene (20 ml) and acetic acid (1 mmol) were added and the mixture was heated to 110° C. under magnetic stirring and reacted for 14 hours. TLC monitors the reaction, and after the raw material point disappears completely, add 50 milliliters of ethyl acetate and 50 milliliters of saturated aqueous sodium chloride for extraction in the reaction solution, and the organic layer is washed with anhydrous NaCl 2 SO 4 For drying, the dried organic phase was concentrated to dryness under reduced pressure, and then 5 ml of acetone and 5 grams of 100-200 mesh silica gel were added to the concentrated evaporated product, and after stirring evenly, evaporated to dryness under reduced pressure, and the s...
Embodiment 3
[0078] Example 3: Synthesis of N-benzyl-2-(benzylamino)-6-fluoro-3-nitroquinoline-4-formamide (compound 3)
[0079] In a 25-mL round-bottom flask, add N,N'-dibenzyl-2-nitroethylene-1,1-diamine (1 mmol) and 5-fluoroindoline-2,3-dione ( 1.1 mmol), xylene (15 ml) and acetic acid (2 mmol) were added and heated to 120° C. under magnetic stirring, and reacted for 2 hours. TLC monitors the reaction, and after the raw material point disappears completely, 50 milliliters of ethyl acetate and 50 milliliters of saturated aqueous sodium chloride are added to the reaction solution for extraction, and the organic layer is washed with anhydrous NaCl. 2 SO 4 For drying, the dried organic phase was concentrated to dryness under reduced pressure, and then 2 ml of acetone and 2 g of 100-200 mesh silica gel were added to the concentrated evaporated product, stirred evenly, evaporated to dryness under reduced pressure, and the sample was loaded with petroleum ether / ethyl acetate The eluent of es...
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