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Synthesis method of benzo [a] pyrrolo [3, 4-c] carbazole-1, 3 (2H, 8H)-diketone compound

A synthetic method, 4-c technology, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, many reaction steps, cumbersome operations, etc., and achieve the effects of mild reaction conditions, easy operation, and avoiding environmental pollution

Inactive Publication Date: 2021-01-08
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In view of the importance of this class of compounds, people have studied and developed a variety of methods for the synthesis of benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione compounds, but These developed methods have disadvantages such as many reaction steps, harsh reaction conditions, expensive raw materials, and cumbersome operations, which limit the application of these reactions in actual production.

Method used

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  • Synthesis method of benzo [a] pyrrolo [3, 4-c] carbazole-1, 3 (2H, 8H)-diketone compound
  • Synthesis method of benzo [a] pyrrolo [3, 4-c] carbazole-1, 3 (2H, 8H)-diketone compound
  • Synthesis method of benzo [a] pyrrolo [3, 4-c] carbazole-1, 3 (2H, 8H)-diketone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011]

[0012] Add 1a (97mg, 0.5mmol), 2a (83mg, 0.75mmol), toluene (3mL), dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer in sequence to a 15mL pressure tube (15mg, 0.025mmol) and copper acetate (182mg, 1mmol), then the pressure tube was sealed and placed 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, 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 ( 23 mg, 15%). The characterization data of this compound are as follows: 1 H NMR (600MHz, DMSO-d 6 ): δ3.04(s, 3H), 7.34(t, J=7.2Hz, 1H), 7.54(t, J=7.2Hz, 1H), 7.68(d, J=7.8Hz, 1H), 7.70-7.75 (m, 2H), 8.55(d, J=7.8Hz, 1H), 8.80(d, J=7.8Hz, 1H), 8.84(d, J=7.8Hz, 1H), 12.79(s, 1H). 13 C NMR (150MHz, DMSO-d 6 )δ: 23.9, 112.2, 118.0, 121.1, 121.6, 122.8, 123.2, 124.4, 125.1, 125.2, 126.3, 127.0, 128.0, 128.1, ...

Embodiment 2

[0014] Add 1a (97mg, 0.5mmol), 2a (83mg, 0.75mmol), toluene (3mL), dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer in sequence to a 15mL pressure tube (15mg, 0.025mmol) and copper acetate monohydrate (200mg, 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, 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 ( 27 mg, 18%).

Embodiment 3

[0016] Add 1a (97mg, 0.5mmol), 2a (83mg, 0.75mmol), toluene (3mL), dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer in sequence to a 15mL pressure tube (15mg, 0.025mmol) and silver acetate (167mg, 1mmol), then the pressure tube was sealed and placed 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, 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 ( 45 mg, 30%).

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Abstract

The invention discloses a synthesis method of a benzo [a] pyrrolo [3, 4-c] carbazole-1, 3 (2H, 8H) diketone compound, and belongs to the technical field of organic synthesis. According to the technical scheme, the preparation method is characterized by comprising the following steps: dissolving a 2-aryl indole compound 1 and an N-substituted maleimide compound in a solvent, adding a catalyst and an oxidant, and reacting at 80-120 DEG C to obtain the target product benzo [a] pyrrolo [3, 4-c] carbazole-1, 3 (2H, 8H)-diketone compound. The target product benzo [a] pyrrolo [3, 4-c] carbazole-1, 3(2H, 8H)-diketone compound is prepared through [4 + 2] oxidative cyclization reaction between the 2-aryl indole compound and the N-substituted maleimide compound, and the method has the advantages ofsimplicity and convenience in operation, mild conditions, wide substrate application range and the like, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-diketone compounds. Background technique [0002] Benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione is an important class of nitrogen-containing fused heterocyclic compounds with anticancer, antitumor, antibacterial, anti Viruses, anti-angiogenesis and other biological activities. For example, 1,11-dichloro-12-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2- base)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione is an antibiotic drug, 5 , 6,7-trimethoxybenzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione is an angiogenesis inhibitor, 6-(2-( Dimethylamino)ethyl)-3-hydroxynaphtho[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,14H)-dione can inhibit the growth of cancer cells, 7-Methyl-1H-benzo[h]indolo[2,3-a]pyrrolo[3,4-c]carbazole-6,8(7H,15H)-dione can be used a...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 沈娜娜郭琛昊范学森张新迎李彬
Owner HENAN NORMAL UNIV
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