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Bis carbonyl indole compound and synthesis method

A technology of biscarbonyl indole and a synthesis method, which is applied in the field of organic compound technology application, can solve problems such as application hindrance and toxicity, and achieve the effects of high reaction efficiency, mild reaction conditions and easy preparation.

Active Publication Date: 2015-08-05
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although traditional acid chloride reagents have been used to construct some dicarbonyl structures, there are some obstacles to the application of such strategies due to their toxicity and sensitivity.

Method used

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  • Bis carbonyl indole compound and synthesis method
  • Bis carbonyl indole compound and synthesis method
  • Bis carbonyl indole compound and synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of Compound 1ab:

[0044]

[0045] The catalyst CuTC (0.02mmol, 10mol%) and α-hydroxyacetophenone 1a (0.2mmol, 1equiv., 27.2mg) and 1-methylindole 1b (0.6mmol, 78.7mg) were added to the reaction tube, and then added After the reaction solvent benzene (4 mL), the reaction was stirred at a reaction temperature of 80° C. for 6 hours in an oxygen atmosphere. After monitoring the reaction by thin-layer chromatography, the product 1ab (43.4mg) yield was obtained after direct column chromatography separation: 83%;1 H NMR (400MHz, CDCl 3 )δ8.53–8.42(m,1H),8.10(dd,J=5.1,3.4Hz,2H),7.80(s,1H),7.67–7.58(m,1H),7.49(t,J=7.7Hz ,2H),7.43–7.36(m,3H),3.83(s,3H); 13 C NMR (100MHz, CDCl 3 )δ193.7, 187.5, 139.5, 137.7, 134.2, 133.5, 130.3, 128.7, 126.4, 124.2, 123.5, 122.7, 112.9, 109.9, 33.7. MS (EI) m / z 263 (M + ).

Embodiment 2

[0047] Synthesis of compound 2ab:

[0048]

[0049] The catalyst CuTC (0.02mmol, 10mol%) and α-hydroxyacetophenone 1a (0.2mmol, 1equiv., 27.2mg) and 1-allylindole 2b (0.6mmol, 94.8mg) were added in the reaction tube, and then After adding the reaction solvent benzene (4 mL), the reaction was stirred at a reaction temperature of 80° C. for 6 hours in an oxygen atmosphere. After the end of the reaction was monitored by thin-layer chromatography, product 2ab (39.6 mg) was obtained after direct column chromatography separation. Yield: 69%; 1 H NMR (400MHz, CDCl 3 )δ8.55–8.45(m,1H),8.16–8.07(m,2H),7.85(s,1H),7.67–7.59(m,1H),7.49(dd,J=10.6,4.8Hz,2H) ,7.42–7.33(m,3H),6.05–5.91(m,1H),5.25(ddd,J=17.8,13.7,0.8Hz,2H),4.75(dt,J=5.6,1.4Hz,2H); 13 C NMR (100MHz, CDCl 3 )δ193.6, 187.6, 138.5, 137.1, 134.2, 133.4, 131.4, 130.3, 128.7, 126.5, 124.2, 123.5, 122.7, 119.3, 113.1, 110.4, 49.7. HRMS (EI) Calcd for C 19 h 15 NO 2 289.1103,Found 289.1102.

Embodiment 3

[0051] Synthesis of compound 3ab:

[0052]

[0053] The catalyst CuTC (0.02mmol, 10mol%) and α-hydroxyacetophenone 1a (0.2mmol, 1equiv., 27.2mg) and 1-benzyl indole 3b (0.6mmol, 124.2mg) were added to the reaction tube, and then added After the reaction solvent benzene (4 mL), the reaction was stirred at a reaction temperature of 80° C. for 6 hours in an oxygen atmosphere. After the end of the reaction was monitored by thin-layer chromatography, product 3ab (47.8 mg) yield was obtained after direct column chromatography separation: 71%; 1 H NMR (400MHz, CDCl 3 )δ8.51(d,J=7.8Hz,1H),8.18–8.06(m,2H),7.92(s,1H),7.67–7.59(m,1H),7.50(t,J=7.7Hz,2H ),7.38(m,1H),7.36–7.27(m,5H),7.20–7.13(m,2H),5.33(s,2H); 13 C NMR (100MHz, CDCl 3 )δ193.5,187.6,138.8,137.2,135.1,134.2,133.4,130.3,129.1,128.7,128.3,127.0,126.6,124.3,123.5,122.8,113.3,110.6,51.1. 23 h 17 NO 2 339.1259, Found 339.1262.

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Abstract

The present invention discloses a method for double carbonylation of indole, wherein alpha-hydroxyketone and indole are adopted as reaction raw materials, oxygen is adopted as an oxidizing agent, and a reaction is performed in benzene at a temperature of 80 DEG C under the effect of a copper catalyst to obtain the bis carbonyl indole compound represented by a formula (III). According to the present invention, advantages of high efficiency of the reaction, high yield, application of the oxygen as the oxidizing agent, mild reaction conditions, no requirement of strong acid and strong alkali, catalysis with the cheap metal, easy reaction substrate preparation, and reaction amplification achieving are provided.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a class of biscarbonylindole compounds and a synthesis method thereof. Background technique [0002] Dicarbonyl compounds not only widely exist in a series of natural products with unique activities, but also can be used as important synthons to transform into a variety of fluorescent materials. For example, quinoxaline structures substituted by aromatic heterocycles can be conveniently prepared from biscarbonyl compounds, and such structures have many applications as photoinitiators and fluorescent ion detectors. Although traditional acyl chloride reagents have been used to construct some dicarbonyl structures, the application of such strategies has been hindered due to their toxicity and sensitivity. At the same time, fluorescent materials containing indole skeletons have attracted more and more attention in recent years due to their ...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07D405/06C07D409/06C07D403/04C07D405/14C07D409/14C09K11/06
CPCC07D209/12C07D403/04C07D405/06C07D405/14C07D409/06C07D409/14C09K11/06C09K2211/1044C09K2211/1088C09K2211/1092
Inventor 姜雪峰张泽光代志洪
Owner EAST CHINA NORMAL UNIV
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