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Method for preparing 3,4-dihydroisoquinoline-2(1H)-one compound through photocatalytic micro-channel

A ketone compound, dihydroquinoline technology, applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc., can solve expensive fluorine sources and transition metal catalysts, many synthesis steps, environmental problems Unfriendly and other problems, to achieve the effect of improving reaction yield, high reaction yield, and simple construction

Active Publication Date: 2019-08-09
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthetic methods commonly used to introduce fluorine atoms in organic compounds often have the disadvantages of requiring expensive fluorine sources and transition metal catalysts.
(W.-J.Chung, C.-D.Vanderwal, Angew.Chem.Int.Ed.2016, 55, 4396-4434.) The traditional preparation of quinolines often has many synthetic steps, serious energy waste, Unfriendly to the environment and many other disadvantages, these disadvantages tend to limit its application in industrial development, so there is a need to develop an efficient method for preparing quinoline

Method used

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  • Method for preparing 3,4-dihydroisoquinoline-2(1H)-one compound through photocatalytic micro-channel
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  • Method for preparing 3,4-dihydroisoquinoline-2(1H)-one compound through photocatalytic micro-channel

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Experimental program
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Effect test

Embodiment 1

[0055] (E)-4-(Chloro(phenyl)methylene)-3-methyl-1-toluenesulfonyl-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinone Synthesis of Lin-2(1H)-ones. Take 83mg of 1a (0.2mmol, 1eq), 10-methyl-9-mesitylylacridine perchlorate (5mol% of 1a) was dissolved in 1mL of acetonitrile, sodium trifluoromethanesulfinate (0.6mmol , 3eq), N-chlorophthalimide (0.24mmol, 1.2eq) was dissolved in 1mL of acetonitrile, the above solutions were added to the syringe and pumped into the microchannel reactor using a syringe pump, the inner diameter of the reactor was 0.5mm, The volume was 1 mL, the reaction residence time was 36 s, irradiated with 50 W blue light with a wavelength of 455 nm, and the temperature was controlled at 25 ° C. After the reaction, post-treatment was performed to obtain 101.8 mg of the final product, with a yield of 98%. The characterization data are as follows: 1 H NMR (500MHz, CDCl 3 )δ7.90(d, J=8.0Hz, 2H), 7.81(d, J=8.0Hz, 2H), 7.54(t, J=7.7Hz, 1H), 7.49–7.42(m, 3H), 7.39– 7.34(m,...

Embodiment 2

[0057] (E)-4-(Chloro(phenyl)methylene)-3-methyl-1-toluenesulfonyl-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinone Synthesis of Lin-2(1H)-ones. Take 83mg of 1a (0.2mmol, 1eq), 10-methyl-9-mesitylylacridine perchlorate (19mol% of 1a) was dissolved in 0.2mL of acetonitrile, sodium trifluoromethylsulfinate (1mmol , 5eq), N-chlorophthalimide (1mmol, 5eq) was dissolved in 3mL of acetonitrile, the above solutions were added to the syringe and pumped into the microchannel reactor using a syringe pump, the inner diameter of the reactor was 1mm, and the length was 1m. The reaction residence time was 60s, irradiated with 60W blue light with a wavelength of 455nm, and the temperature was controlled at 55°C. After the reaction, post-treatment was carried out to obtain 92.5mg of the final product, with a yield of 89%.

Embodiment 3

[0059] (E)-4-(Chloro(phenyl)methylene)-3-methyl-1-toluenesulfonyl-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinone Synthesis of Lin-2(1H)-ones. Take 83mg of 1a (0.2mmol, 1eq), terpyridyl ruthenium dichloride hexahydrate (5mol% of 1a) was dissolved in 1mL of 1,2-dichloroethane, sodium trifluoromethylsulfinate (0.6mmol, 3eq) , tetrabutylammonium chloride (0.24mmol, 1.2eq) was dissolved in 1mL of acetonitrile, the above solutions were added to the syringe and pumped into the microchannel reactor with a syringe pump, the inner diameter of the reactor was 0.5mm, and the volume was 1mL. The residence time was 36s, irradiated with 12W blue light with a wavelength of 455nm, and the temperature was controlled at 25°C. After the reaction, post-treatment was carried out to obtain 100.6 mg of the final product, with a yield of 97%.

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Abstract

The invention discloses a method for preparing a 3,4-dihydroisoquinoline-2(1H)-one compound through a photocatalytic micro-channel. The 3,4-dihydroisoquinoline-2(1H)-one compound is efficiently synthesized in one step through a visible light induced tandem radical dual-functionalized reaction. A related reaction device makes a photocatalytic reaction technology combined with a micro-flow-field reaction technology, and the problems that the illumination of a traditional photocatalytic reactor is not uniform, a transfer medium is poor in heat transfer, the reaction time is long and energy is wasted are solved. The reaction device is easy to construct, reaction components are cheap and easy to obtain, and the method has the foundation of industrial amplification.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a photocatalytic microchannel reaction device for preparing 3,4-dihydroquinolin-2(1H)-one compounds by cyclization reaction of 1,7-enyne and its synthesis method . Background technique [0002] One of the most important heterocycles of quinoline is widely found in natural products, pharmaceutical intermediates and functional materials. The commonly used synthetic method is to decompose the six-membered ring into different fragments and then combine them, such as [4+2], [3+3], [2+2+2] and other synthetic methods such as cycloaddition. (a.G.K. Surya Prakash, A.K. Yudin, Chem. Rev. 1997, 97, 757-786; b. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR1-PR43; c. O. A. Tomashenko, V.V. Grushin, Chem. Rev. 2011,111,4475-4521.) As an important class of atoms, fluorine atoms widely exist in human pharmaceutical intermediates and organic synthesis. The commonly used synthetic methods for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227C07D311/12B01J19/00
CPCC07D215/227C07D311/12B01J19/0093
Inventor 郭凯袁鑫郑明卫邱江凯崔玉声庄凯强覃龙州
Owner NANJING UNIV OF TECH
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