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A kind of method that organocatalytic isatin self-condensation prepares isoindigo compounds

A technology of isoindigo and self-condensation, applied in organic chemistry and other directions, can solve the problems of high cost, cumbersome operation, complicated and lengthy synthesis route, etc., and achieve the effects of low toxicity, safe and simple operation, and simple post-processing process.

Active Publication Date: 2021-04-16
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic route requires two kinds of reaction substrates at the same time, the synthetic route is complex and lengthy, the operation is cumbersome, and the cost is high

Method used

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  • A kind of method that organocatalytic isatin self-condensation prepares isoindigo compounds
  • A kind of method that organocatalytic isatin self-condensation prepares isoindigo compounds
  • A kind of method that organocatalytic isatin self-condensation prepares isoindigo compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Under an inert gas atmosphere, add a stirring bar, 0.5 mmol of isatin, 0.05 mmol of DBU, and 2 mL of acetonitrile into the autoclave, then fill the autoclave with carbonyl sulfide gas of about 0.8 MPa, and stir at 25 ° C for 24 After 1 hour, the autoclave was opened, and the reaction solution in the autoclave was dissolved in 2 milliliters of dichloromethane and transferred to a 50-ml round-bottom single-necked flask, with (3 × 2 milliliters) dichloromethane flushing autoclave, The crude product was then obtained after removal of the solvent in vacuo. The crude product was separated and purified by washing with acetone, methanol and dichloromethane. The yield was 98%. The structure of the reaction product is as follows:

[0023] Red solid. 1 H NMR (400MHz, DMSO-d6) δ10.90(s, 2H), 9.05(d,

[0024] J=7.1Hz, 2H), 7.34(s, 2H), 6.96(t, J=7.5Hz, 2H), 6.84(d, J=6.6Hz, 2H); 13 C

[0025] NMR (126MHz, DMSO) δ169.0, 144.2, 133.4, 132.7, 129.4, 121.8, 121.2, 109.6.

Embodiment 2

[0027] Under an inert gas atmosphere, add a stirring bar to the autoclave, 0.5 mmol of 5-methylisatin, 0.05 mmol of DBU, and 2 mL of acetonitrile, then fill the autoclave with carbonyl sulfide gas of about 0.1 MPa, at 100 After stirring at ℃ for 24 hours, the autoclave was opened, and the reaction solution in the autoclave was dissolved in 2 milliliters of dichloromethane and transferred to a 50-ml round-bottom single-necked flask with (3×2 milliliters) dichloromethane The crude product was obtained after flushing the autoclave and removing the solvent in vacuo. The crude product was separated and purified by washing with acetone, methanol and dichloromethane. The yield was 88%. The structure of the reaction product is as follows:

[0028] Dark red solid. 1 H NMR (400MHz, DMSO-d 6 )δ10.73(s, 2H), 8.89(s, 2H), 7.15(d, J=7.9Hz, 2H), 6.73(d, J=7.9Hz, 2H), 2.26(s, 6H); 13 C NMR (101MHz, DMSO-d 6 )δ169.6, 142.4, 133.9, 133.2, 130.1, 122.6, 109.6, 21.3.

Embodiment 3

[0030] Under an inert gas atmosphere, add stirring bar in autoclave, the 5-methoxyisatin of 0.5mmol, the DBU of 0.05 mmol, the acetonitrile of 2mL, then fill into the carbonyl sulfide gas of about 1.2MPa in autoclave, in After stirring for 24 hours at 50°C, the autoclave was opened, and the reaction solution in the autoclave was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round-bottom single-necked flask, and washed with (3×2 ml) dichloromethane Flushing the autoclave with methane and removing the solvent in vacuo gave the crude product. The crude product was separated and purified by washing with acetone, methanol and dichloromethane. The yield was 73%. The structure of the reaction product is as follows:

[0031] Blue-green solid. 1 H NMR (400MHz, DMSO-d 6 )δ10.69(s,2H),8.85(d,J=2.2Hz,2H),6.97(dd,J=8.4,2.4Hz,2H),6.75(d,J=8.5Hz,2H), 3.73( s,6H); 13 C NMR (101MHz, DMSO) δ168.7, 153.9, 137.8, 133.6, 122.1, 118.4, 115.4, 109.2, 55.4.

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Abstract

The invention discloses a method for preparing isoindigo compounds by organically catalyzing the self-condensation of isatin, and relates to the technical fields of organic synthesis, dyes, medicine and chemical industry, and organic photoelectric materials. In the method, isatin and its derivatives are used as raw materials, organic amines are used as catalysts, carbonyl sulfide is passed through, and the functionalized isoindigo compound is prepared under the condition of 25-100 degrees centigrade and stirring for 8-24 hours. The reaction has the characteristics of mild reaction conditions, simple operation, good functional group tolerance, high conversion rate, high yield, and good chemoselectivity. Application prospect.

Description

technical field [0001] The invention relates to a method for preparing isoindigo compounds by organically catalyzing isatin self-condensation, and belongs to the technical fields of organic synthesis, molecular devices, dyes, pharmaceutical chemicals, organic photoelectric materials and the like. Background technique [0002] Isoindigo compounds are a very important class of organic molecular frameworks, which play an important role in medicine, dyes, and molecular devices. For example, methylisoindigo compounds have been used in the clinical treatment of chronic myeloid leukemia (Xiao Z, Hao Y, Liu B, Qian L. Leukocyte Lymph. 2002, 43, 1763; Xiao Z, Wang Y, LuL, et al. al.Leukocyte Res.2006,30,54); the iso-indigo conjugated polymer constructed by Zhou Chunshan et al. is used to make semiconductor materials (Zhou Chunshan; Zhao Jianwen; Cui Zheng. Iso-indigo conjugated polymer, semiconductor CNT Ink, its preparation method and application [P]. Chinese patent: CN10715311A, 2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34
CPCC07D209/34
Inventor 周辉陈伟吕小兵
Owner DALIAN UNIV OF TECH
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