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Polysubstituted indole bithiophene and derivative and synthesis method thereof

A synthetic method and 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, cheap and easy-to-obtain reaction raw materials, and reducing environmental pollution

Active Publication Date: 2017-10-10
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, which require multi-step synthesis processes to complete, and need to add transition metal catalysts, stoichiometric metal oxidants, etc.

Method used

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  • Polysubstituted indole bithiophene and derivative and synthesis method thereof
  • Polysubstituted indole bithiophene and derivative and synthesis method thereof
  • Polysubstituted indole bithiophene and derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-46

[0089] Step 1: Add indole compounds (see Table 1 for specific substances), alkene (alkynes, ketones) compounds (see Table 1 for specific substances) and sulfur powder into the reaction vessel, and add Bronsted acid (see Table 1 for specific substances) ) solution can also be added to the reaction vessel in the container respectively to Bronsted acid (see Table 1 for specific substances) and organic solvent (see Table 1 for specific substances);

[0090] Step 2: The reaction vessel is evenly heated (such as heating in an oil bath) to the temperature described in Table 1, and the indole compounds, alkene (yne, ketone) compounds and sulfur powder are reacted in a solvent, and continue in Table 1. the time mentioned;

[0091] Step 3: Purification step

[0092]Table 1: Indole compound, alkene (alkyne, ketone) compound, Bronsted acid, indole compound, alkene (alkyne, ketone) compound, sulfur powder and Bronsted acid in embodiment 1-46 Molar ratio, reaction temperature and reaction...

Embodiment 1

[0100] The nuclear magnetic data of embodiment 1 product is as follows:

[0101] 1H NMR (100MHz, CDCl3, ppm): δ7.80 (d, J = 7.8Hz, 1H), 7.64–7.62 (m, 3H), 7.37 (dd, J = 15.7, 7.7Hz, 3H), 7.31–7.27 (m,1H),7.25–7.23(m,1H),7.21–7.17(m,1H),3.85(s,3H);13C NMR(100MHz,ppm):δ144.1,142.0,135.78,135.73,129.0,126.6 ,125.1,123.5,122.2,122.0,119.6,119.4,114.3,109.1,32.4.

Embodiment 2

[0102] The nuclear magnetic data of embodiment 2 product is as follows:

[0103] 1H NMR (100MHz, CDCl3, ppm): δ = 7.78 (d, J = 7.8, 1H), 7.55 (s, 1H), 7.51 (d, J = 8.2, 2H), 7.33–7.31 (m, 1H), 7.29–7.25(m,1H),7.20–7.16(m,3H),3.81(s,3H),2.36(s,3H);13C NMR(100MHz,CDCl3,ppm):δ143.8,142.0,136.5,136.0, 133.0, 129.6, 125.1, 123.5, 122.2, 121.9, 119.5, 119.3, 113.7, 109.1, 32.3, 21.2.

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Abstract

The invention relates to polysubstituted indole bithiophene and a derivative and a synthesis method thereof. The technical scheme which is adopted for the first time includes that indole compounds, alkene, alkyne and ketone compounds and sulfur powder are converted into 2-substituted thieno[2,3-b]indole and the derivative in an air atmosphere under catalysis of Bronsted acid, and a product and additional products stable in molecular structure and excellent in chemical property are obtained, raw reaction materials are cheap and easy to acquire without pretreatment, and high reaction atom economy is achieved; the reaction only requires utilization of cheap Bronsted acid, so that environment pollution abatement, raw material saving and reaction cost reduction are realized; the whole reaction system is simple, reaction conditions are mild, a small quantity of reaction devices are adopted, and simplicity and convenience in experiment operation and extensive material sources are realized.

Description

technical field [0001] The invention relates to a multi-substituted indolothiophene and its derivatives and a synthesis method thereof, belonging to the technical field of organic compound synthesis. Background technique [0002] Thieno[2,3-b]indole and its derivatives are an important class of aromatic heterocyclic compounds, which contain a large conjugated system and strong intramolecular electron transfer in the molecule. This special rigid fused ring structure The thieno[2,3-b]indole compounds exhibit many unique properties and biological activities, and have potential applications in many fields such as optoelectronic materials, dyes, medicine, and supramolecular recognition. The existing methods for synthesizing such compounds have the disadvantages of complex synthesis steps, multi-step synthesis processes, and the addition of transition metal catalysts and stoichiometric metal oxidants. Contents of the invention [0003] In order to fill the gap in the prior art,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 邓国军倪鹏辉肖福红黄华文谭静
Owner XIANGTAN UNIV
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