Multi-substituted 6-aryl benzo [a] carbazole, derivatives thereof, synthesizing method of multi-substituted 6-aryl benzo [a] carbazole

An arylbenzene, multi-substitution technology, applied in the field of organic compound synthesis, can solve problems such as complex synthesis steps, achieve the effects of saving raw materials, excellent chemical properties, and reducing environmental pollution

Active Publication Date: 2019-03-01
XIANGTAN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Existing methods for synthesizing such compounds have complicated synthesis steps, and transition metals such as palladium, ruthenium, rhodium, and copper are often used as catalysts, and multi-step synthesis processes can only be completed, and it is often necessary to pre-functionalize the starting materials and add chemically equivalent metals Disadvantages such as oxidizing agents

Method used

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  • Multi-substituted 6-aryl benzo [a] carbazole, derivatives thereof, synthesizing method of multi-substituted 6-aryl benzo [a] carbazole
  • Multi-substituted 6-aryl benzo [a] carbazole, derivatives thereof, synthesizing method of multi-substituted 6-aryl benzo [a] carbazole
  • Multi-substituted 6-aryl benzo [a] carbazole, derivatives thereof, synthesizing method of multi-substituted 6-aryl benzo [a] carbazole

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Experimental program
Comparison scheme
Effect test

Embodiment 1-55

[0059] Step 1: 2-arylindole compounds (see Table 1 for specific substances) and aromatic acetylenic compounds or aromatic ketones (see Table 1 for specific substances) are added in the reaction vessel, and iodine-containing compounds (see Table 1 for specific substances) 1) the solution of adding in the reaction vessel also can contain iodine compound (see Table 1 for concrete substance) and organic solvent (see Table 1 for concrete substance) in container respectively;

[0060] Step 2: uniformly heat the reaction vessel (such as oil bath heating) to the temperature described in Table 1, 2-arylindole compound and aromatic alkyne compound or aromatic ketone compound are reacted in a solvent, and continue to show The time described in 1; the reaction that needs to be explained does not require the atmosphere environment to participate in the reaction, so the atmosphere can be air or inert gas, nitrogen, etc. It can be reacted as long as it is not in a strong oxidizing atmosphere...

Embodiment 1

[0070] The nuclear magnetic data of embodiment 1 product is as follows:

[0071] 1 H NMR (400MHz, CDCl 3 , ppm) δ8.87(s, 1H), 8.10-8.08(m, 1H), 7.99-7.96(m, 1H), 7.69-7.67(m, 2H), 7.57-7.50(m, 7H), 7.44( d, J=8.0Hz, 1H), 7.35(t, J=7.6Hz, 1H), 7.04(t, J=7.6Hz, 1H).; 13 C NMR (100MHz, ppm) δ141.2, 138.6, 136.5, 135.2, 132.0, 129.3, 128.8, 128.3, 127.6, 125.6, 125.4, 124.6, 123.8, 122.0, 120.8, 120.3, 120.1, 119.5, 110.9

Embodiment 2

[0072] The nuclear magnetic data of embodiment 2 product is as follows:

[0073] 1 H NMR (400MHz, CDCl 3 , ppm) δ8.83 (s, 1H), 8.09-8.07 (m, 1H), 7.98-7.95 (m, 1H), 7.58 (d, J=7.9 Hz, 2H), 7.54-7.50 (m, 4H) , 7.48(s, 1H), 7.37-7.34(m, 3H), 7.05(t, J=7.6Hz, 1H), 2.50(s, 3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ138.6, 138.2, 137.2, 136.5, 135.2, 132.1, 129.2, 129.0, 128.8, 125.6, 125.3, 124.5, 123.9, 122.1, 120.8, 120.3, 120.1, 119.5, 116.8, 114.8,

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Abstract

The invention relates to a multi-substituted 6-aryl benzo [a] carbazole, derivatives thereof, a synthesizing method of the multi-substituted 6-aryl benzo [a] carbazole. According to the synthesizing method of the multi-substituted 6-aryl benzo [a] carbazole, for the first time under catalysis of iodine compounds and in an air atmosphere, 2-aryl indole compounds, aromatic alkyne compounds or aromatic ketone compounds are converted into the multi-substituted 6-aryl benzo [a] carbazole and the derivatives thereof to prepare products and by-products, which are stable in molecular structure and excellent in chemical properties; reaction materials are low in price and easy to acquire and save pretreatment; reaction is high in atom economy and simple in operation and can be promoted through low-price iodine compounds, thereby being low in environmental pollution and reaction costs; the entire reaction system is simple, mild in reaction conditions, few in reaction equipment, simple and safe and experimental operation and rich and wide in material resources.

Description

technical field [0001] The invention relates to a multi-substituted 6-aryl benzo[a]carbazole and its derivatives and a synthesis method thereof, belonging to the technical field of organic compound synthesis. Background technique [0002] 6-Arylbenzo[a]carbazole and its derivatives are an important class of nitrogen-containing fused aromatic heterocompounds, which contain a large conjugated system and strong intramolecular electron transfer in the molecule. This special rigidity The fused ring structure enables 6-arylbenzo[a]carbazole compounds to exhibit many unique properties and biological activities, and has potential applications in many fields such as optoelectronic materials, dyes, medicine, and supramolecular recognition. Existing methods for synthesizing such compounds have complicated synthesis steps, mostly using transition metals such as palladium, ruthenium, rhodium, and copper as catalysers, and a multi-step synthesis process can only be completed, and it is of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80
CPCC07D209/80
Inventor 邓国军倪鹏辉谭静肖福红黄华文
Owner XIANGTAN UNIV
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