Synthesis method of benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound

A technology of pyridyl imidazole and a synthetic method, which is applied in directions such as organic chemistry, and achieves the effects of simple and convenient reaction operation, wide application range, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2021-01-05
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no relevant report on the synthesis method of this type of compound at present, so the simple and efficient synthesis of benzo[e]pyridylimidazo[4,5-g]isoindole-1,3(2H)-dione compounds is developed The new method has important research and application value

Method used

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  • Synthesis method of benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound
  • Synthesis method of benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound
  • Synthesis method of benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound

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Experimental program
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Effect test

Embodiment 1

[0011]

[0012] Add 1a (97mg, 0.5mmol), 2a (83mg, 0.75mmol), ethanol (3mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer in sequence to a 15mL pressure tube (15mg, 0.025mmol) and copper acetate (182mg, 1mmol), then seal the pressure tube and place it in an oil bath at 100°C for 20h. After the reaction was completed, cool to room temperature, filter the organic phase with diatomaceous earth and spin dry the organic phase, and separate the crude product through a silica gel column (petroleum ether / ethyl acetate=5 / 1, v / v) to obtain a yellow solid product 3a ( 17mg, 11%). The characterization data of this compound are as follows: 1 H NMR (600MHz, CF 3 CO 2 D) δ: 3.48(s, 3H), 7.90(t, J=7.2Hz, 1H), 8.13-8.16(m, 2H), 8.30(d, J=9.0Hz, 1H), 8.43(t, J= 7.8Hz,1H),8.69(dd,J 1 =6.6Hz,J 2 =3.0Hz,1H),9.39(dd,J 1 =6.6Hz,J 2 =3.0Hz,1H),10.67(d,J=6.6Hz,1H). 13 C NMR (150MHz, CF 3 CO 2 D) δ: 23.3, 111.9, 117.7, 118.7, 119.7, 122.2, 123.0, 126.1, 126.3, 127.4, 131.9, 131...

Embodiment 2

[0014] Add 1a (97mg, 0.5mmol), 2a (83mg, 0.75mmol), tetrahydrofuran (3mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer in sequence to a 15mL pressure tube (15mg, 0.025mmol) and copper acetate (182mg, 1mmol), then seal the pressure tube and place it in an oil bath at 100°C for 20h. After the reaction was finished, cool to room temperature, filter the organic phase with diatomaceous earth, spin dry the organic phase, and separate the crude product through a silica gel column (petroleum ether / ethyl acetate=5 / 1, v / v) to obtain a yellow solid product 3a ( 6mg, 4%).

Embodiment 3

[0016] Add 1a (97mg, 0.5mmol), 2a (83mg, 0.75mmol), acetonitrile (3mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer in sequence to a 15mL pressure tube (15mg, 0.025mmol) and copper acetate (182mg, 1mmol), then seal the pressure tube and place it in an oil bath at 100°C for 20h. After the reaction was finished, cool to room temperature, filter the organic phase with diatomaceous earth, spin dry the organic phase, and separate the crude product through a silica gel column (petroleum ether / ethyl acetate=5 / 1, v / v) to obtain a yellow solid product 3a ( 35mg, 23%).

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Abstract

The invention discloses a synthesis method of a benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound, and belongs to the technical field of organic synthesis. According to the technicalscheme, the preparation method is characterized by comprising the following steps: dissolving a 2-arylimidazole[1,2-a]pyridine compound and an N-substituted maleimide compound in a solvent, adding a catalyst and an oxidant, and reacting at 80 to 120 DEG C to obtain the target product benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound. The target product benzo[e]pyridylimidazole[4,5-g]isoindole-1,3(2H)-diketone compound is prepared from simple and easily prepared raw materials through transition metal catalyzed [4 + 2] oxidative cyclization reaction, so that heterocyclic structural units such as pyridylimidazole and maleimide are fused together to directly obtain a pentacyclic aromatic system; the whole synthesis process is simple, efficient, convenient to operate, mild in condition and wide in substrate application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of benzo[e]pyridylimidazol[4,5-g]isoindole-1,3(2H)-dione compounds. Background technique [0002] Maleimide derivatives widely exist in natural organic molecules and occupy an important position in the field of medicinal chemistry. Many organic molecules containing this structural unit have shown good biological and pharmaceutical activities, such as inhibiting HIV protease, anti-cancer, anti-tuberculosis and anti-fungal, etc. On the other hand, pyridimidazole is not only the basic skeleton of many antiviral, antibacterial, anticancer and nerve tissue stimulating drugs, but also widely used in the fields of biological probes, fluorescent dyes and optoelectronic materials, showing broad application prospects . The benzo[e]pyridylimidazo[4,5-g]isoindole-1,3(2H)-dione synthesized by the present invention is two important structural units of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C07D495/22
CPCC07D471/14C07D495/22
Inventor 沈娜娜郭琛昊范学森张新迎李彬杨玉洁
Owner HENAN NORMAL UNIV
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