Indolo [2, 3-b] indole derivative and synthesis method thereof

A 3-b, derivative technology, applied in the direction of organic chemistry, can solve problems such as complex synthesis steps, and achieve the effect of simple reaction system, stable molecular structure, and easy application expansion

Active Publication Date: 2021-04-02
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing method for synthesizing this type of compound has complicated synthesis steps and requires a multi-step synthesis process to complete, and there are also disadvantages such as the need to add transition metal catalysts, stoichiometric metal oxidants, and the use of relatively high-activity starting materials.

Method used

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  • Indolo [2, 3-b] indole derivative and synthesis method thereof
  • Indolo [2, 3-b] indole derivative and synthesis method thereof
  • Indolo [2, 3-b] indole derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Example 1 5-methyl-6-phenyl-5,6-dihydroindolo[2,3 -b ] Synthesis of Indole

[0109]

[0110]Take a reaction tube, add 0.04 mmol (8.8 mg) trimethylsulfoxide iodide, 0.2 mmol (45.4 mg) 2-(3-(1-methyl) indole) cyclohexanone, 0.3 mmol (27.3 μL) Aniline, 1.0 mmol (71.0 μL) dimethyl sulfoxide, 0.5 mL toluene were sealed and stirred at 140°C for reaction. After 16 hours of reaction, 41.5 mg of pure product was obtained by conventional treatment with a yield of 70%.

[0111] According to the operation method of embodiment 1, the present invention has synthesized following compound:

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] The NMR, high-resolution mass spectrum and other characterization data of the compounds of some embodiments of the present invention are given below:

[0120] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0121] 1 H NMR (400 MHz, CDCl3) δ 7.98 (t, J = 6.8 Hz, 2H), 7.6...

Embodiment 2

[0122] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0123] 1 H NMR (400 MHz, CDCl 3 ) δ 7.97 (t, J = 6.8 Hz , 2H), 7.52-7.45 (m,3H), 7.43 (d, J = 7.4 Hz, 1H), 7.34-7.29 (m, 3H), 7.25-7.22 (m, 1H), 7.14 (t, J = 7.6 Hz, 1H), 6.97 (d, J = 8.2 Hz, 1H), 3.41 (s, 3H), 2.05 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 145.1, 140.8, 140.0, 137.9, 135.8, 131.4, 129.6, 129.5,127.4, 122.0, 120.8, 120.3 119.9, 119.7, 118.3 110.3 109.2,100.6, 17.5; HRMS (ESI) M / Z: [ M+H] + calcd for C 22 h 19 N 2 + 311.1543; found311.1542.

Embodiment 3

[0124] The NMR and mass spectrum data of embodiment 3 product are as follows:

[0125] 1 H NMR (400 MHz, CDCl 3 ) δ 7.91 (d, J = 7.6 Hz, 2H), 7.72 (d, J = 7.4Hz, 1H), 7.70-7.64 (m, 1H), 7.58 (d, J = 4.4 Hz, 2H), 7.32-7.26 (m, 2H), 7.23-7.18 (m, 2H), 7.16-7.10 (m, 4H), 7.09-7.03 (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 145.0, 141.5, 141.4, 140.0, 137.8, 134.3 131.6, 130.5, 129.7, 128.8,128.5, 128.1, 127.9, 122.2, 121.8, 120.8, 120.0, 119.9, 119.5, 118.4, 118.2,110.5, 109.0, 100.9, 29.9; HRMS (ESI) m / z: [M+H] + calcd for C 27 h 21 N 2 + 373.1699; found 373.1700.

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Abstract

The invention mainly relates to indolo [2, 3b] indole, a derivative thereof and a synthesis method thereof. According to the technical scheme, during synthesis, a metal catalyst is not required to beused, and a 2-(3-indolyl) cyclohexanone compound and an aniline compound are converted into a polysubstituted indolo [2, 3-b] indole derivative under the action of an iodine reagent and in an organicsolvent. According to the method, the problems that an existing synthesis method of the functionalized indolo [2, 3-b] indole compound is complex in synthesis step, a multi-step synthesis process needs to be adopted for completing the synthesis, a metal catalyst or peroxide needs to be used, and raw materials are difficult to prepare are solved; the atom economy is maintained to the greatest extent; and the derivative also has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple experimental operation, wide material sources, high yield, easyexpansion of users and application, high product utilization value, expectable market commercialization prospect and the like.

Description

technical field [0001] The present invention relates to a kind of indolo[2,3 -b ] The invention relates to indole derivatives and a synthesis method thereof, which belong to the technical field of organic synthesis. Background technique [0002] Indoloindole is an important skeleton structure of many drugs and drug intermediates, organic electrochemical devices, and organic light-emitting materials, and is widely used in the fields of organic light-emitting semiconductors, drugs, and optoelectronic materials. Therefore, the synthetic method of indoloindole derivatives has been widely paid attention to. The existing methods for synthesizing such compounds have complex steps and require multi-step synthesis processes to complete, and there are also disadvantages such as the need to add transition metal catalysts, stoichiometric metal oxidants, and the use of relatively high-activity starting materials. Contents of the invention [0003] For above-mentioned situation, the o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 邓国军姜平宇陈善平黄华文肖福红
Owner XIANGTAN UNIV
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