Substituted tetrahydroquinoline derivative, hydrolysis product thereof, synthetic method and application thereof

A technology of hydrolyzed products and derivatives, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of high price, inability to recycle and reuse, etc., and achieve the effect of green reaction, environmental friendliness and good antibacterial activity

Active Publication Date: 2015-10-14
日照新睿招商发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Commonly used visible light catalysts are complexes of Ru and Ir and organic dyes. However, these catalysts have many disadvantages compared to homogeneous catalysts, such as expensive and cannot be recycled and reused.

Method used

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  • Substituted tetrahydroquinoline derivative, hydrolysis product thereof, synthetic method and application thereof
  • Substituted tetrahydroquinoline derivative, hydrolysis product thereof, synthetic method and application thereof
  • Substituted tetrahydroquinoline derivative, hydrolysis product thereof, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of Titanium Dioxide(P25) / NiO Catalyst

[0029] Add 1 g of commercially available titanium dioxide (P25) into 100 mL of nickel acetylacetonate solution (the concentration of the solution is 5×10 -4 mol / L, the proportioning ratio of solvent is ethanol:n-hexane=1:5v / v), stirred at room temperature for 24h, filtered, washed with a small amount of ethanol, then dried at 80°C for 4h, and then placed in a muffle furnace at 500°C Calcined for 1 h to obtain the desired modified titanium dioxide catalyst. Adjust the ratio of nickel in the composite catalyst by repeating the above-mentioned steps, three kinds of catalysts P25 / NiO(1), P25 / NiO(2), P25 / NiO(3) are obtained, wherein the mass percentages of nickel ions are respectively 2.3%, 6.5%, 10.6%.

Embodiment 2

[0031] Visible-light-catalyzed cyclization of N,N-dimethylaniline and 4-chlorophenylmaleimide.

[0032] 0.130g (0.625mmol) of 4-chlorophenylmaleimide, N, N-dimethylaniline 0.151g (1.25mmol), the P25 / NiO (3) (1mol%) catalyst of 0.01g is added pyrex test tube In the test tube, 25ml of acetonitrile was added and dissolved by ultrasound. Then illuminate for 12h under 3W LED blue light. After the reaction was completed, the reaction mixture was concentrated and the product was separated by silica gel column chromatography, using petroleum ether (b.p.60-90°C)-ethyl acetate as eluent for gradient elution. Compound 1 represented by formula III was obtained with a yield of 62%.

[0033] Compound detection results:

[0034] Melting point: mp 188-190°C; 1 H NMR (CDCl 3 , 400MHz) δ2.83(s, 3H), 3.10(dd, 1H, J=11.4, 4.2Hz), 3.53(ddd, 1H, J=7.2, 4.4, 2.8Hz), 3.60(dd, 1H, J= 11.4, 2.6Hz), 4.15(d, 1H, J=9.6Hz), 6.74(dd, 1H, J=8.2, 0.6Hz), 6.91(td, 1H, J=7.4, 1.1Hz), 7.22-7.26 (m, 3H), 7...

Embodiment 3

[0042] Visible-light-catalyzed cyclization of N,N-dimethylaniline and N-tert-butylmaleimide.

[0043] N-tert-butylmaleimide 0.096g (0.625mmol), N, N-dimethylaniline 0.151g (1.25mmol), 0.01g of P25 / NiO (3) (1mol%) catalyst was added to pyrex In the test tube, add 25ml of acetonitrile to the test tube and dissolve by ultrasonic. Then illuminate for 12h under 3W LED blue light. After the reaction was completed, the reaction mixture was concentrated and the product was separated by silica gel column chromatography, using petroleum ether (b.p.60-90°C)-ethyl acetate as eluent for gradient elution. Compound 2 represented by formula IV was obtained with a yield of 69%.

[0044] Compound detection results:

[0045] Melting point: mp 76-78°C; 1 H NMR (CDCl 3 , 400MHz) δ1.54(s, 9H), 2.80(s, 3H), 3.00(dd, 1H, J=11.2, 4.4Hz), 3.21(ddd, 1H, J=7.6, 4.4, 3.0Hz), 3.43 (dd, 1H, J=11.4, 3.0Hz), 3.83(d, 1H, J=9.6Hz), 6.71(d, 1H, J=8.0Hz), 6.88(td, 1H, J=7.6, 1.2Hz) , 7.21 (td, 1H, J=8.2, 1...

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PUM

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Abstract

The invention provides a substituted tetrahydroquinoline derivative and a hydrolysis product thereof, and provides a method of preparing the above-mentioned compound with visible-light-responding surface-modified titanium dioxide catalyst and an application of the tetrahydroquinoline derivative and the hydrolysis product thereof in the fields of antibacterial medicines. The compound in the invention is wide in anti-bacterial activity, is prepared with the surface-modified titanium dioxide, which is low in cost and easy to obtain and is stable and toxic-free, as the catalyst, so that the tetrahydroquinoline compound can be synthesized with visible light, is green in reactions and is environment-friendly. In addition, by means of introduction of other active groups into a tetrahydroquinoline ring, new tetrahydroquinoline derivative having the anti-bacterial activity can be prepared.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a substituted tetrahydroquinoline derivative, in particular to a preparation method for visible light catalytic synthesis of a substituted tetrahydroquinoline derivative based on modified P25. Background technique [0002] In recent years, visible-light-induced photoredox catalysis has attracted extensive attention as an efficient and versatile method for the functionalization of relatively inactive C–H in the nitrogen neighbourhood. Commonly used visible light catalysts are complexes of Ru and Ir and organic dyes. However, compared with homogeneous catalysts, these catalysts have many disadvantages, such as expensive, and cannot be recycled and reused. [0003] Titanium dioxide (P25) as a highly efficient photocatalyst has received extensive attention in recent years, but the absorption of P25 in the visible light region is very weak, and its catalysis is mainly carried out under...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D215/54A61P31/04
CPCC07D215/54C07D471/04
Inventor 沈永淼唐剑梁学正陶菲菲肖慧泉邵颖何宁德
Owner 日照新睿招商发展有限公司
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