Dihydropyrazino[2,3-b]indole, pyrazino[2,3-b]indole compounds, synthesis method and application

A technology of dihydropyrazine and 3-b, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of complex raw material synthesis, poor substrate universality, low reaction yield, etc., and achieve wide application foreground effect

Active Publication Date: 2019-08-02
ZHEJIANG UNIV
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Problems solved by technology

These methods for synthesizing pyrazino[2,3-b]indole and quinoxalino[2,3-b]indole skeletons are old, and there are also problems such as poor universality of substrates for the reaction, complex synthesis of raw materials, and reaction products. Disadvantages such as low rate

Method used

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  • Dihydropyrazino[2,3-b]indole, pyrazino[2,3-b]indole compounds, synthesis method and application
  • Dihydropyrazino[2,3-b]indole, pyrazino[2,3-b]indole compounds, synthesis method and application
  • Dihydropyrazino[2,3-b]indole, pyrazino[2,3-b]indole compounds, synthesis method and application

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Experimental program
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Effect test

Embodiment 1

[0021] The following steps were used: Add N-methyl-3-diazo-2-p-toluenesulfonylimide indole (65mg, 0.2mmol), 2,3-diphenyl-2H-azimine to a 25mL reaction tube (58mg, 0.3mmol), rhodium dimer octanoate (3mg, 0.004mmol), sealed and evacuated, and replaced the air with nitrogen to make the reaction take place under nitrogen atmosphere. Finally, cumene (2 mL) was added, and the reaction was placed in an oil bath at 100° C. for 12 hours. After the reaction, the reaction mixture was cooled to room temperature, the solvent was removed by a rotary evaporator, and then separated by column chromatography to obtain 87 mg of a yellow product with a yield of 89%. Melting point 153.5–154.6°C; 1 H NMR (400MHz, CDCl 3 )δ7.85(d,J=8.0Hz,1H),7.52–7.50(m,2H),7.36–7.28(m,7H),7.23–7.15(m,6H),6.81(d,J=8.4Hz ,2H),6.28(s,1H),3.78(s,3H),2.23(s,3H); 13 C NMR (100MHz, CDCl 3 )δ151.87,144.80,137.02,135.42,134.49,133.18,129.71,129.19,128.69,128.61,128.16,127.77,127.02,126.32,123.41,122.65,122.07,120.64,12...

Embodiment 2

[0024] The following steps were used: Add N-ethyl-3-diazo-2-p-toluenesulfonimide indole (68mg, 0.2mmol), 2,3-diphenyl-2H-azimine to a 25mL reaction tube (58mg, 0.3mmol), rhodium trifluoroacetate (0.004mmol), sealed and evacuated, and replaced the air with nitrogen to make the reaction take place under nitrogen atmosphere. Finally xylene (2 mL) was added and the reaction was placed in an oil bath at 100°C for 12 hours. After the reaction, the reaction mixture was cooled to room temperature, the solvent was removed by a rotary evaporator, and then separated by column chromatography to obtain 88 mg of a yellow product with a yield of 87%. Melting point 73.3–74.6°C; 1 H NMR (400MHz, CDCl 3 )δ7.86(d,J=7.6Hz,1H),7.52–7.50(m,2H),7.38–7.25(m,7H),7.22–7.16(m,6H),6.82(d,J=8.0Hz ,2H),6.30(s,1H),4.63–4.54(m,1H),4.27–4.18(m,1H),2.45(s,3H),0.96(t,J=7.2Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ152.60,144.74,136.96,134.43,134.09,133.06,129.77,129.17,128.66,128.55,128.17,127.90,127.06,126.29,125...

Embodiment 3

[0027]The following steps were used: Add N-isopropyl-3-diazo-2-p-toluenesulfonylimide indole (71 mg, 0.2 mmol), 2,3-diphenyl-2H-ethyleneimine to a 25 mL reaction tube Reaction (58mg, 0.3mmol) and rhodium octanoate (3mg, 0.004mmol) were sealed and evacuated, and the air was replaced with nitrogen to allow the reaction to take place under a nitrogen atmosphere. Finally dichloroethane (2 mL) was added, and the reaction was placed in an oil bath at 100° C. for 12 hours. After the reaction, the reaction mixture was cooled to room temperature, the solvent was removed by a rotary evaporator, and then separated by column chromatography to obtain 65 mg of a yellow product with a yield of 63%. Melting point 175.4–176.5°C; 1 H NMR (400MHz, CDCl 3 )δ7.85–7.83(m,1H),7.55–7.52(m,3H),7.35–7.28(m,5H),7.23–7.16(m,7H),6.82(d,J=8.0Hz,2H) ,6.30(s,1H),5.11–5.00(m,1H),2.25(s,3H),1.86(d,J=6.8Hz,3H),1.04(d,J=7.2Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ152.86,144.72,137.10,134.41,133.21,133.07,129.77,1...

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Abstract

The invention discloses dihydropyrazine [2,3-b] indole, pyrazine [2,3-b] indole compounds as well as a synthesis method and application. The method comprises the following steps: preparing a dihydropyrazine [2,3-b] indole intermediate from 3-diazonium-2-imine indole and 2(i)H( / i)-azirine as raw materials and a rhodium octanoate dimer as a catalyst; aromizing the intermediate under an alkaline condition, so as to obtain a series of pyrazine [2,3-b] indole compounds. In order to simplify the steps of an experiment, a one-pot two-step method is adopted, so that the synthesizing efficiency of the pyrazine [2,3-b] indole compounds is greatly improved. The synthetic route has the advantages of being simple and convenient in operation, mild in conditions and wide in universality of substrates, being economic and efficient, and so on. The pyrazine [2,3-b] indole compounds have potential application in the aspects of medicines and organic optoelectronic materials, in particular to hole-transport materials.

Description

technical field [0001] The invention relates to dihydropyrazino[2,3-b]indole, pyrazino[2,3-b]indole compounds, their synthesis method and application. Background technique [0002] In recent years, with the further increase of human demand for energy, the development of new energy sources and the research of new materials have become the direction of scientists' efforts, and energy materials with pyrazine structures are gradually being recognized by people. We found that pyrazino[2,3-b]indole is a kind of good fluorescent chromophore, which not only has good photoluminescence performance in solution state, but also has excellent photoluminescence efficiency in solid state. There are not many reports on the synthesis of pyrazino[2,3-b]indole skeletons (Tetrahedron Lett., 1993, 34, 2953–2956; Tetrahedron, 1998, 54, 11095–11110), and some Indolediones and o-aryl diamines are a method for the synthesis of quinoxalino[2,3-b]indole skeletons as raw materials (J.HeterocyclicChem.,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06
CPCC07D487/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044
Inventor 吕萍王彦广丁华龙
Owner ZHEJIANG UNIV
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