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Benzo[f]quinoline derivatives catalyzed and synthesized by multiple catalysts

A catalyst and solvent technology, applied in the field of synthesis of benzo[f]quinoline derivatives, achieves the effects of high yield, simple operation and low price

Inactive Publication Date: 2015-06-17
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a number of convenient routes to the synthesis of nitrogen heterocyclic structures have been developed using some Lewis acids and Brenster acids to catalyze the imino Diels-Alder reaction, there is still a lot of room for development of this method.

Method used

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  • Benzo[f]quinoline derivatives catalyzed and synthesized by multiple catalysts
  • Benzo[f]quinoline derivatives catalyzed and synthesized by multiple catalysts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1 In a 100ml three-necked flask, add 1mmol of p-nitrobenzaldehyde, 1mmol of 1-naphthylamine, 1.1mmol of butynedioic acid dimethyl, 0.1mmol of SnCl 2 With 6ml of acetonitrile, react for a certain period of time under reflux conditions, and the reaction time is detected by TLC. After the reaction was completed, it was washed twice with 20 ml of water and once with 20 ml of saturated brine, dried over anhydrous sodium sulfate for 12 hours, suction filtered, and rotary evaporated. through a silica gel column (V 石油醚 :V 乙酸乙酯 =1:2~1:10), the product 3-(4-nitrophenyl)benzo[f]quinoline-1,2-dicarboxylic acid dimethyl ester / 3-(4-nitrophenyl )-3,4-dihydrobenzo[f]quinoline-1,2-dicarboxylic acid dimethyl ester, orange and dark yellow solid.

[0013] m.p.: 115~116℃. 1 H NMR (DMSO-d 6 , 400MHz): δ H 1.06(t, J=7.2Hz, 3H, CH 3 ), 1.36(t, J=7.2Hz, 3H, CH 3 ), 7.83~7.86(m, 2H, ArH), 7.92(d, J=8.8Hz, 2H, ArH), 8.06(d, J=8.8Hz, 1H, ArH), 8.20~8.22(m, 1H, ArH ), 8.30~8.32(m, ...

Embodiment 2

[0019] Example 2 Add 1mmol of m-chlorobenzaldehyde, 1mmol of 1-naphthylamine, 1.1mmol of butynedioic acid dimethyl ester, 0.1mmol of [BMIM] BF to a 100ml three-necked flask. 4 With 6ml of acetonitrile, react for a certain period of time under reflux conditions, and the reaction time is detected by TLC. After the reaction was completed, it was washed twice with 20 ml of water and once with 20 ml of saturated brine, dried over anhydrous sodium sulfate for 12 hours, suction filtered, and rotary evaporated. through a silica gel column (V 石油醚 :V 乙酸乙酯 =1:2~1:10), the product 3-(3-chlorophenyl)benzo[f]quinoline-1,2-dicarboxylic acid dimethyl ester / 3-(3-chlorophenyl)- Dimethyl 3,4-dihydrobenzo[f]quinoline-1,2-dicarboxylate, light yellow and dark yellow solid.

[0020] m.p.: 143~144℃. 1 H NMR (DMSO-d 6 , 400MHz): δ H 3.74 (s, 3H, CH 3 ), 4.08 (s, 3H, CH 3 ), 7.56~7.64(m, 3H, ArH), 7.73(s, 1H, ArH), 7.83~7.84(m, 2H, ArH), 8.07(d, J=9.2Hz, 1H, ArH), 8.19~8.21 (m, 2H, ArH), 8.35 ...

Embodiment 3

[0026] Example 3 Add 1mmol of p-fluorobenzaldehyde, 1mmol of 1-naphthylamine, 1.1mmol of butynedioic acid dimethyl ester, 0.1mmol of [BMIMHSO 3 ] HSO 4 With 6ml of acetonitrile, react for a certain period of time under reflux conditions, and the reaction time is detected by TLC. After the reaction was completed, it was washed twice with 20 ml of water and once with 20 ml of saturated brine, dried over anhydrous sodium sulfate for 12 hours, suction filtered, and rotary evaporated. through a silica gel column (V 石油醚 :V 乙酸乙酯 =1:2~1:10), the product 3-(4-fluorophenyl)benzo[f]quinoline-1,2-dicarboxylic acid dimethyl ester / 3-(4-fluorophenyl)- Dimethyl 3,4-dihydrobenzo[f]quinoline-1,2-dicarboxylate, orange and dark yellow solid.

[0027] m.p.: 165~167℃. 1 H NMR (DMSO-d 6 , 400MHz): δ H 3.72 (s, 3H, CH 3 ), 4.00 (s, 3H, CH 3 ), 7.55(t, J=8.4Hz, 2H, ArH), 7.69~7.73(m, 2H, ArH), 7.85~7.88(m, 2H, ArH), 8.10(d, J=9.2Hz, 1H, ArH ), 8.28~8.30(m, 2H, ArH), 8.43(d, J=9.2Hz, 1H, ArH)...

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Abstract

A synthesis method of benzo[f]quinoline derivatives is provided; through various substituted aromatic aldehydes, 1-naphthylamine and dimethyl acetylenedicarboxylate, and under action of SnCl2, [BMIM]BE4, [BMIMHSO3]HSO4, [BMIMHSO3]H2PO4, [HMIM]Cl, [BMIM]HSO4, [HMIM]HSO4 and aminosulfonic acid as catalysts, a one-pot reaction is carried out, and a series of benzo[f]quinoline compounds are generated.

Description

technical field [0001] The invention belongs to the field of organic synthesis, with SnCl 2 , sulfamic acid and various ionic liquids ([BMIM]BF 4 , [BMIMHSO 3 ] HSO 4 , [BMIMHSO 3 ]H 2 PO 4 , [HMIM]Cl, [BMIM]HSO 4 、[HMIM]H8O 4 ) as a catalyst to specifically design the synthesis of benzo[f]quinoline derivatives. Background technique [0002] Multicomponent reactions play an important role in modern organic synthesis. Multicomponent reactions are commonly used in one-pot methods, showing high atom economy and high selectivity. Multicomponent reactions produce fewer by-products than classical stepwise synthetic routes. At the same time save a lot of time and solvent. [0003] The synthesis of benzoquinoline derivatives has become the focus of interest of many chemists. Because it has been reported that benzoquinoline derivatives have broad-spectrum biological activity properties, such as antibacterial activity, uridine diphosphotransferase activity, antimicrobial ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/10
CPCC07D221/10
Inventor 臧洪俊严青冯稼轩于建春陆海程博闻
Owner TIANJIN POLYTECHNIC UNIV
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