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Polysubstituted 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and derivative thereof and synthesis method thereof

A multi-substitution and derivative technology, applied in organic chemistry and other directions, can solve the problems of complex synthesis steps, and achieve the effect of saving raw materials, reducing reaction costs, and stabilizing molecular structure.

Active Publication Date: 2018-12-14
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing methods for synthesizing such compounds have complex synthesis steps, mostly using organic selenium compounds or metal selenium compounds as selenium sources, which can only be completed by multi-step synthesis processes, and often need to add transition metal catalysts, chemically equivalent metal oxidants, etc.

Method used

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  • Polysubstituted 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and derivative thereof and synthesis method thereof
  • Polysubstituted 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and derivative thereof and synthesis method thereof
  • Polysubstituted 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and derivative thereof and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-51

[0060] Step 1: 2-arylindole compound (see Table 1 for specific substances), aromatic ketone compound (see Table 1 for specific substances) and selenium powder are added in the reaction vessel, and the iodine-containing compound (see Table 1 for specific substances) The solution is added in the reaction vessel and can also contain iodine compound (see Table 1 for specific substances) and organic solvent (see Table 1 for specific substances) in the container respectively;

[0061] Step 2: The reaction vessel is evenly heated (such as oil bath heating) to the temperature described in Table 1, 2-arylindole compounds, aromatic ketone compounds and selenium powder are reacted in a solvent, and continue in Table 1 the time mentioned;

[0062] Step 3: Purification step

[0063] Table 1: 2-aryl indole compound, aromatic ketone compound, iodine-containing compound, organic solvent, (2-aryl indole compound, aromatic ketone compound, selenium powder and iodine-containing compound in embo...

Embodiment 1

[0071] The nuclear magnetic data of embodiment 1 product is as follows:

[0072] 1 H NMR (400MHz, CDCl 3 , ppm) δ7.90-7.88 (m, 1H), 7.59 (s, 1H), 7.55-7.53 (m, 1H), 7.44 (d, J=8.6 Hz, 2H), 7.32-7.19 (m, 8H) , 7.13-7.09(m, 1H), 3.75(s, 3H); 13 C NMR (100MHz, ppm) δ141.7, 141.2, 139.1, 137.3, 134.0, 131.6, 130.5, 128.2, 127.9, 127.8, 127.4, 125.7, 125.7, 124.1, 123.9, 122.1, 120.3, 120.65, 110.0, 110.0 .

Embodiment 2

[0073] The nuclear magnetic data of embodiment 2 product is as follows:

[0074] 1 H NMR (400MHz, CDCl 3 , ppm) δ7.71(s, 1H), 7.48(s, 1H), 7.45-7.42(m, 3H), 7.32-7.24(m, 6H), 7.11(t, J=7.4Hz, 1H), 7.03 (d, J=8.1Hz, 1H), 3.76(s, 3H), 2.42(s, 3H); 13 CNMR (100MHz, CDCl 3 , ppm) δ141.4, 139.4, 139.0, 137.2, 134.1, 133.6, 131.6, 130.4, 128.1, 127.8, 127.7, 126.1, 125.7, 125.6, 125.3, 122.1, 120.3, 119.9, 110.6, 139.5, 109.5

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Abstract

The invention relates to polysubstituted 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and a derivative thereof and a synthesis method thereof. A technical scheme comprising that 2-arylindoles, aromaticketones and selenium powder are converted into 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and the derivative thereof under the catalysis of iodine compounds and in an air atmosphere is adopted for the first time, and the product and the additional product thereof with stable molecular structure and excellent chemical properties are prepared; the technical scheme comprises that the 2-arylindoles,aromatic ketones and selenium powder are converted into polysubstituted 3-(3-benzo[b]selenophenyl)-1H-2-aryl indole and the derivative thereof under the catalysis of iodine compounds and in an air atmosphere, the reaction raw materials are cheap and easy to obtain and have no need of pretreatment, and the atomic economy of the reaction is high; the reaction only needs to use cheap iodine compounds, environmental pollution is reduced, the raw materials are saved, and the reaction cost is reduced; the whole reaction system is simple, the reaction conditions are mild, the number of reaction equipment is small, experiment operation is simple and safe, and material sources are wide.

Description

technical field [0001] The invention relates to a multi-substituted 3-(3-benzo[b]selenophenyl)-1H-2-arylindole and a derivative thereof and a synthesis method thereof, belonging to the technical field of organic compound synthesis. Background technique [0002] 3-(3-Benzo[b]selenophenyl)-1H-2-arylindole and its derivatives are an important class of aromatic heterocyclic compounds, which contain large conjugated systems and strong molecular Internal electron transfer, this special rigid fused ring structure enables 3-(3-benzo[b]selenophenyl)-1H-2-arylindole compounds to exhibit many unique properties and biological activities. , dyes, medicine, supramolecular recognition and many other fields have potential applications. The existing methods for synthesizing such compounds have the disadvantages of complicated synthesis steps, mostly using organic selenium compounds or metal selenium compounds as the selenium source, which can only be completed by multi-step synthesis proces...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D421/04C07D421/14C07D517/04
CPCC07D421/04C07D421/14C07D517/04
Inventor 邓国军倪鹏辉谭静赵文奇肖福红
Owner XIANGTAN UNIV
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