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Method for efficiently preparing quinoline derivative from titanocene dichloride in cooperation with with sulfo-benzoic acid in water phase

A technology of sulfobenzoic acid and titanocene dichloride, applied in the direction of organic chemistry, etc., to achieve the effect of mild reaction conditions, short reaction time and simple operation

Inactive Publication Date: 2016-04-06
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of quinoline derivatives, and provide a method for preparing quinoline derivatives with simple operation, mild reaction conditions, green and high efficiency

Method used

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  • Method for efficiently preparing quinoline derivative from titanocene dichloride in cooperation with with sulfo-benzoic acid in water phase
  • Method for efficiently preparing quinoline derivative from titanocene dichloride in cooperation with with sulfo-benzoic acid in water phase
  • Method for efficiently preparing quinoline derivative from titanocene dichloride in cooperation with with sulfo-benzoic acid in water phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Taking the preparation of the compound diethyl-2,6-dimethyl-1,2-dihydroquinoline-2,4-dicarboxylic acid of the following formula as an example, the raw materials used and the preparation method are as follows:

[0013]

[0014] Add 0.0125g (0.05mmol) titanocene dichloride, 38μL (0.10mmol) 4-sulfophthalic acid, 0.1072g (1mmol) 4-methylaniline, and 329μL (3mmol) pyruvic acid to a 10mL Shrek tube Ethyl acetate and 1 mL of distilled water were stirred for 6 hours at 60°C. The reaction was stopped, and 10-15 mL of ethyl acetate was added for extraction. After the ethyl acetate was removed by rotary evaporation of the organic layer, it was separated and purified by silica gel column (eluent was ethyl acetate The volume ratio with petroleum ether is 1:10) to obtain diethyl-2,6-dimethyl-1,2-dihydroquinoline-2,4-dicarboxylic acid with a yield of 90% , The spectral data of the product is as follows:

[0015] 1 HNMR(400MHz, CDCl 3 )δ: 7.61(s, 1H), 6.88(d, J=7.5Hz, 1H), 6.65(s, 1H), 6.5...

Embodiment 2

[0018] Taking the preparation of the compound diethyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylic acid of the following formula as an example, the raw materials used and the preparation method are as follows:

[0019]

[0020] In Example 1, the 4-methylaniline used was replaced with an equimolar amount of aniline, and the other steps were the same as in Example 1, to obtain diethyl-2-methyl-1,2-dihydroquinoline-2, The yield of 4-dicarboxylic acid is 89%. The spectrum data of the product is as follows:

[0021] 1 HNMR(400MHz, CDCl 3 )δ: 7.71 (dd, J = 7.9, 1.0 Hz, 1H), 6.99 (dd, J = 7.7, 1.2 Hz, 1H), 6.65 (d, J = 0.6 Hz, 1H), 6.60-6.51 (m, 2H) ), 4.42(s, 1H), 4.26(dd, J=7.1, 1.3Hz, 2H), 4.18-4.01(m, 2H), 1.47(s, 3H), 1.30(t, J=7.1Hz, 3H) , 1.19 (t, J=7.1 Hz, 3H).

[0022] 13 CNMR(101MHz, CDCl 3 )δ: 172.87, 164.84, 141.58, 131.46, 128.55, 127.51, 125.49, 117.55, 115.55, 113.18, 60.77, 59.98, 57.49, 26.40, 13.23, 13.10.

Embodiment 3

[0024] Taking the preparation of the compound diethyl-6-methoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylic acid of the following formula as an example, the raw materials used and the preparation method thereof are as follows:

[0025]

[0026] In Example 1, the 4-methylaniline used was replaced with an equimolar amount of 4-methoxyaniline, and the other steps were the same as in Example 1, to obtain diethyl-6-methoxy-2-methyl- The yield of 1,2-dihydroquinoline-2,4-dicarboxylic acid is 92%. The spectral data of the product is as follows:

[0027] 1 HNMR(400MHz, CDCl 3 )δ: 7.49 (d, J=2.8Hz, 1H), 6.74 (s, 1H), 6.70 (dd, J=8.6, 2.8Hz, 1H), 6.58 (d, J=8.6Hz, 1H), 4.38- 4.27 (m, 3H), 4.23-4.11 (m, 2H), 3.74 (s, 3H), 1.52 (s, 3H), 1.37 (s, 3H), 1.24 (s, 3H).

[0028] 13 CNMR(101MHz, CDCl 3 )δ: 175.46, 167.34, 142.05, 135.55, 134.09, 130.46, 130.00, 127.11, 118.00, 115.65, 63.08, 62.32, 59.93, 29.68, 28.58, 17.25, 15.66.

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Abstract

The invention discloses a method for efficiently preparing quinoline derivative from titanocene dichloride in cooperation with with sulfo-benzoic acid in a water phase. According to the method, aromatic amine and pyruvate are used as raw materials, water serves as the solvent, the titanocene dichloride serves as the catalyst, and under the synergistic promotion effect of the sulfo-benzoic acid, the quinoline derivative can be prepared efficiently. Through the method, the dosage of the catalyst is small, the price is low, toxicity is avoided, reaction conditions are mild, reaction time is short, atom economy is high, product yield is high, a new low-cost environment-friendly efficient way is developed for preparation of the quinoline derivative, and the prepared quinoline derivative has huge application potential in preparation of medicine, natural products and organic synthesis intermediates.

Description

Technical field [0001] The invention relates to a method for efficiently preparing quinoline derivatives in aqueous phase with sulfobenzoic acid ligands in cooperation with titanocene dichloride. Background technique [0002] In the research, it is found that many types of heterocyclic compounds have certain biological activity, and quinoline compounds are a more common type of heterocyclic compounds with pharmacological and biological activity. Quinoline, the parent of quinoline derivatives, was first isolated from coal tar by Runge. Soon after quinoline was separated from coal tar, people used alkali dry distillation of antimalarial drug quinine (Qulnine) to obtain quinoline. Studies have shown that many compounds containing quinoline rings have antibacterial, anti-bacterial, anti-allergic, anti-malarial, anti-tumor, anti-cancer, anti-hypertensive, anti-depression and memory-enhancing biological and pharmacological activities. In recent years, quinolines Derivatives are also ...

Claims

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Application Information

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IPC IPC(8): C07D215/50C07D221/10
CPCC07D215/50C07D221/10
Inventor 高子伟罗艳龙陈禧孙华明张伟强张国防吴亚王璟王秀
Owner SHAANXI NORMAL UNIV
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