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A method for efficiently preparing quinoline derivatives with sulfobenzoic acid in cooperation with titanocene dichloride in aqueous phase

A technology of sulfobenzoic acid and titanocene dichloride, applied in organic chemistry and other directions, to achieve the effect of high atom economy, mild reaction conditions and great application potential

Inactive Publication Date: 2018-05-08
SHAANXI NORMAL UNIV
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  • Summary
  • 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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  • A method for efficiently preparing quinoline derivatives with sulfobenzoic acid in cooperation with titanocene dichloride in aqueous phase
  • A method for efficiently preparing quinoline derivatives with sulfobenzoic acid in cooperation with titanocene dichloride in aqueous phase
  • A method for efficiently preparing quinoline derivatives with sulfobenzoic acid in cooperation with titanocene dichloride in aqueous phase

Examples

Experimental program
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Effect test

Embodiment 1

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

[0013]

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

[0015] 1 H NMR (400MHz, CDCl 3 )δ: 7.61(s, 1H), 6.88(d, J=7.5Hz, 1H), 6.65(s, 1H), 6.54(d, J=8.0Hz, 1H), 4.50(...

Embodiment 2

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

[0019]

[0020] In Example 1, the 4-methylaniline used is replaced with aniline in an equimolar amount, and other steps are the same as in Example 1 to obtain diethyl-2-methyl-1,2-dihydroquinoline-2, 4-dicarboxylic acid, its productive rate is 89%, and the spectral data of product is as follows:

[0021] 1 H NMR (400MHz, CDCl 3 )δ: 7.71(dd, J=7.9, 1.0Hz, 1H), 6.99(dd, J=7.7, 1.2Hz, 1H), 6.65(d, J=0.6Hz, 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 C NMR (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 of the following formula diethyl-6-methoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylic acid as an example, the raw materials used and its preparation method are as follows:

[0025]

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

[0027] 1 H NMR (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 C NMR (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 an aqueous phase catalyzed by sulfobenzoic acid ligands in cooperation with titanocene dichloride. Background technique [0002] It is found in the research that many heterocyclic compounds have certain biological activities, and quinoline compounds are a relatively common class of heterocyclic compounds with pharmacological activity and biological activity. Quinoline, the parent of quinoline derivatives, was first isolated from coal tar by Runge. Shortly after the separation of quinoline from coal tar, quinoline was also obtained by dry distillation of the antimalarial drug quinine (Qulnine) with alkali. Studies have shown that many compounds containing quinoline rings have biological and pharmacological activities such as antibacterial, bactericidal, antiallergic, antimalarial, antitumor, anticancer, antihypertensive, antidepressant, and memory enhancement. In recen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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