Thieno[3,4-b] indole derivative and synthesis method thereof

A technology for indole derivatives and synthesis methods, applied in the field of thieno[3,4-b]indole derivatives and their synthesis, achieving the effects of mild synthesis reaction conditions, easy availability of raw materials, and good functional group diversity

Active Publication Date: 2020-06-16
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the direct synthesis of thieno[3,4-b]indole, so it is of great significance to develop simple and efficient methods for preparing thienoindole compounds.

Method used

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  • Thieno[3,4-b] indole derivative and synthesis method thereof
  • Thieno[3,4-b] indole derivative and synthesis method thereof
  • Thieno[3,4-b] indole derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] The specific process is: add N,S-1,6-enyne 2a (111mg, 0.3mmol), FeCl 2(8mg, 0.06mmol), elemental sulfur (51mg, 0.2mmol), t-BuOLi (16mg, 0.2mmol), DMF (2mL), react at 80°C for 3 hours. After separation by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate=20:1, v / v), a yellow solid 1a (79 mg, 74%) was obtained, and the target product was obtained by NMR and High-resolution mass spectrometry was confirmed.

[0040] Typical Compound Characterization Data

[0041] 4H-thieno[3,4-b]indole 1a, yellow solid. 1 H NMR (400MHz,D 6 -DMSO)δ11.70(br s,1H,NH),8.00 and 7.74-7.48(m each,2:7H,aromatic CH),7.90(t,J=6.9Hz,3H,aromatic CH),7.42(t, J=7.4Hz, 1H, aromatic CH), 7.14(t, J=7.5Hz, 1H, aromatic CH). 13 C{ 1 H}NMR (100MHz,D 6 -DMSO) δ185.4 (Cq, CO), 150.2, 148.7, 140.9, 133.1, 129.1, 118.6, 107.4 (Cq), 132.2, 130.1, 130.0, 129.2, 128.5, 128.4, 127.8, 121.2, 120.7, 113.2 (aromatic CH).C 23 h 15 HRMS theoretical value of NOS [M+H] + ...

Embodiment 2

[0043]

[0044] The specific process is: add N,S-1,6-enyne 2b (115mg, 0.3mmol), FeCl 2 (8mg, 0.06mmol), elemental sulfur (51mg, 0.2mmol), t-BuOLi (16mg, 0.2mmol), DMF (2mL), react at 80°C for 3 hours. After separation by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate=20:1, v / v), a yellow solid 1b (84 mg, 76%) was obtained, and the target product was obtained by NMR and High-resolution mass spectrometry was confirmed.

[0045] Typical Compound Characterization Data

[0046] Thieno[3,4-b]indole derivative 1b, yellow solid. 1 H NMR (700MHz, 23°C, D 6 -DMSO)δ11.58(br,1H,NH),8.00(d,J=8.7Hz,2H,aromatic CH),7.96–7.72(m,3H,aromatic CH),7.62(t,J=7.6Hz, 2H, aromatic CH), 7.55(dd, J=7.5 and 5.6Hz, 2H, aromatic CH), 7.40(t, J=7.6Hz, 1H, aromatic CH), 7.12(dd, J=12.1 and 5.0Hz, 3H ,aromatic CH),2.02(s,3H,CH 3 ). 13 C{ 1 H}(176MHz,23℃,D 6 -DMSO) δ183.7 (Cq, CO), 162.2 (Cq, C-CH 3 ),149.6,148.2,139.6,118.1 and 106.9(Cq),132.8,131.8,130.2,129.5,1...

Embodiment 3

[0048]

[0049] The specific process is: add N,S-1,6-enyne 2c (115mg, 0.3mmol), FeCl 2 (8mg, 0.06mmol), elemental sulfur (51mg, 0.2mmol), t-BuOLi (16mg, 0.2mmol), DMF (2mL), react at 80°C for 3 hours. After separation by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate=20:1, v / v), a yellow solid 1c (76 mg, 69%) was obtained, and the target product was obtained by NMR and High-resolution mass spectrometry was confirmed.

[0050] Typical Compound Characterization Data

[0051] Thieno[3,4-b]indole derivative 1c, yellow solid. 1H NMR (400MHz, 23°C, D6-DMSO) δ11.67 (br, 1H, NH), 7.98 (m, 2H, aromatic CH), 7.89 (d, J=7.8Hz, 1H, aromatic CH), 7.70 ( m,J=11.3Hz,2H,aromatic CH),7.64(m,1H,aromatic CH),7.59(dd,J=11.4 and 4.5Hz,2H,aromatic CH),7.55(d,J=8.1Hz,1H ,aromatic CH),7.51(t,J=7.6Hz,1H,aromatic CH),7.41(t,J=7.4Hz,1H,aromatic CH),7.37(d,J=7.6Hz,1H,aromatic CH), 7.14(t,J=7.3Hz,1H,aromatic CH),2.43(s,3H,CH3).13C{1H}(100MHz,23℃,D6-DMSO)δ185.1(Cq...

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Abstract

The invention discloses a thieno[3,4-b]indole derivative and a synthesis method thereof. The preparation method comprises the following steps: by taking 4-alkylthio-4-((2-(phenyl ethynyl)aryl)amino)butyl-3-ene-2-one as a raw material, catalyzing a self-cyclization reaction of 4-alkylthio-4-((2-(phenyl ethynyl)aryl)amino)butyl-3-ene-2-one with an oxidizing agent by catalyzing with a cheap metal toconstruct the thieno[3,4-b] indole derivative in one step, wherein the obtained thieno[3,4-b] indole derivative is widely applied to the fields of photoelectric materials, medicines and the like. Themethod of the invention has characteristics of cheap metal catalysis, elemental sulfur oxidation, easily available raw materials, simple operation, high efficiency, wide substrate adaptability and diversified functional groups.

Description

technical field [0001] The invention relates to a thieno[3,4-b]indole derivative and a synthesis method thereof, belonging to the technical field of chemical organic synthesis. Background technique [0002] Thienoindole-containing compounds have a wide range of applications in materials science, medicinal chemistry and synthetic biology, so the synthesis of such compounds has attracted much attention (Acc. Chem. Res. 2014, 47, 1493-1502.). Since the polarizability of sulfur atoms is higher than that of other heteroatoms (such as N, O, etc.), thienoindoles have better absorption properties for light. Among them, thieno[3,4-b]indole is the key structural unit for the construction of organic photovoltaic cells (J.Mater.Chem.A 2017,5,2297-2308.). In the past, the synthesis of thienoindole derivatives was mainly prepared by further cyclization of thiophene or indole rings, but these works required thiophene or indole as starting materials, and pre-functionalization of the starti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 柳竹青余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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