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1,2,3,4-tetrahydroquinoline compound and its synthesis method and application

A technology of tetrahydroquinolines and compounds, applied in organic chemistry, drug combination, diseases, etc., can solve the problems of cumbersome steps, and achieve the effects of simple operation, less environmental pollution, and a wide range of substrates

Inactive Publication Date: 2019-03-22
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods are tedious and require functionalized aniline derivatives as raw materials

Method used

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  • 1,2,3,4-tetrahydroquinoline compound and its synthesis method and application
  • 1,2,3,4-tetrahydroquinoline compound and its synthesis method and application
  • 1,2,3,4-tetrahydroquinoline compound and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of 2-methyl-7-nitro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester:

[0040] Take a 10 mL round bottom flask connected with a reflux condenser, add 2,4-dinitrotoluene (182 mg, 1 mmol), methyl methacrylate (294 mg, 3 mmol) and cesium carbonate (652 mg, 2 mmol), evacuate nitrogen, inject anhydrous THF (5 mL), and heat to 65 o C, reflux for 12 hours. After the reaction, the solvent and excess olefins were removed by rotary evaporation, the remaining solid was washed with sufficient amount of dichloromethane, filtered, and the filter residue was dissolved in sufficient amount of water, then activated carbon was added for decolorization, the solid was filtered off, the solvent was spin-dried, and vacuum-dried to obtain recovered of cesium carbonate. The filtrate containing the product was spin-dried and purified through a silica gel column with dichloromethane as the developing solvent to obtain the target product as a yellow solid with a yield of 213...

Embodiment 2

[0046] Synthesis of butyl 2-methyl-7-nitro-1,2,3,4-tetrahydroquinoline-2-carboxylate:

[0047] The reaction raw materials are 2,4-dinitrotoluene (182 mg, 1 mmol), butyl methacrylate (420 mg, 3 mmol), and the reaction time is 12 hours. Other specific operations are the same as in Example 1. The product was a yellow solid, the yield was 237 mg, and the yield was 81%.

[0048] Product infrared spectrum data: IR (KBr): 3382 cm -1 , 2933 cm -1 , 1728 cm -1 , 1616 cm -1 ,1523 cm -1 , 1454 cm -1 , 1346cm -1 , 1180 cm -1 .

[0049] Product H NMR spectrum data: 1 H NMR (400 MHz, CDCl 3 ) δ 7.48 (dd, J = 8.2, 2.1Hz, 1H, HAr), 7.42 (d, J = 2.1 Hz, 1H, HAr), 7.07 (d, J = 8.3 Hz, 1H, HAr), 4.66 (s, 1H, NH), 4.14 (t, J = 6.6 Hz, 2H, CH 2 ), 2.93-2.68 (m, 2H, CH 2 ), 2.34(dt, J = 13.0, 5.2 Hz, 1H, CH 2 ), 1.90 (ddd, J = 13.2, 10.3, 5.9 Hz, 1H, CH 2 ),1.61 (dd, J = 13.3, 5.5 Hz, 2H, CH 2 ), 1.50 (s, 3H, CH 3 ), 1.33 (dd, J = 15.1,7.5 Hz, 2H, CH 3 ), 0.92 (t, ...

Embodiment 3

[0053] Synthesis of 2,4-dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester:

[0054] The reaction raw materials are 2,4-dinitroethylbenzene (194 mg, 1 mmol), methyl methacrylate (294 mg, 3 mmol), and the reaction time is 12 hours. Other specific operations are the same as in Example 1. The product was a yellow solid, the yield was 191 mg, and the yield was 73%.

[0055] Product infrared spectrum data: IR (KBr): 3383 cm -1 , 2932 cm -1 , 1732 cm -1 , 1603 cm -1 ,1535 cm -1 , 1485 cm -1 , 1345 cm -1 , 1181 cm -1 .

[0056] Product H NMR spectrum data: 1 H NMR (400 MHz, CDCl 3 ) δ 7.87 (d, J = 2.3 Hz,1H, HAr), 7.47 (s, 1H, HAr), 7.03 (d, J = 2.2 Hz, 1H, HAr), 4.96 (s, 1H, NH),3.77(s, 3H, CH 3 ), 3.00 (ddd, J = 16.1, 14.6, 9.5 Hz, 1H, CH 2 ), 2.88 (d, J =8.4 Hz, 3H, CH 3 ), 2.81 (d, J = 26.5 Hz, 1H, CH 2 ), 2.32-1.87 (m, 1H, CH 2 ), 1.60(s, 3H, CH 3 ) ppm.

[0057] Product structural formula:

[0058]

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Abstract

The invention relates to 1,2,3,4-tetrahydroquinoline compound and a synthetic method and application thereof. In a structure formula of the compound, the R1 is nitro or trifluoromethyl or 3-nitrophenylnitrobenzene sulfonyl or cyano, the R2 is hydrogen or methyl, the R3 is methyl formate or butyl formate, and the R4 is methyl. An aromatic ring of the 1,2,3,4-tetrahydroquinoline compound contains a series of electron withdrawing groups. The synthetic method is simple, economical, environment-friendly, easy to operate, easy to control, higher in product purity and yield and good in development prospect in industrial production; in addition, the synthetic method is also a novel synthetic method in atom economy; furthermore, the 1,2,3,4-tetrahydroquinoline compound can serve as intermediate to be used for preparing antagonist medicine.

Description

[0001] This invention was funded by Tianjin Natural Science Foundation (No. 16JCYBJC19700). technical field [0002] The invention belongs to the field of organic synthetic chemistry, and relates to a 1,2,3,4-tetrahydroquinoline compound and a synthesis method and application thereof. Background technique [0003] 1,2,3,4-Tetrahydroquinoline compounds are a very important class of N-heterocyclic aromatic compounds, which play an important role in the construction of the skeleton structure of organic compounds and are the constituents of many natural products (such as tetrahydro quinoline alkaloids) and important building blocks for a wide range of bioactive molecules (see reference: Rakotoson, J. H. et al. Planta Med ,1998, 64 , 762). Tetrahydroquinoline derivatives with complex and variable structures are important components of modern medicines and the source of new drug development. It itself has a variety of biological activities, and can be used for prevention and tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/48C07D471/04A61P15/00
CPCC07D215/48C07D471/04
Inventor 刘桂艳王建辉尹茂聪刘成鑫
Owner TIANJIN NORMAL UNIVERSITY
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