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Method for synthesising carbazole compounds

A technology of compounds and carbazoles, applied in the field of synthesizing functionalized carbazoles, can solve problems such as harsh reaction conditions, poor reaction selectivity, and unfriendly environment, and achieve the effects of easy-to-obtain reagents, mild reaction conditions, and environmental friendliness

Active Publication Date: 2013-04-17
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the simple, fast and efficient synthesis of carbazole and its derivatives.
The limitation is that the raw materials are not easy, the reaction conditions are harsh, the reaction selectivity is poor, and it is not friendly to the environment, etc.

Method used

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  • Method for synthesising carbazole compounds
  • Method for synthesising carbazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add gold trichloride (3.1 mg, 0.01 mmol), 1-(1-ethyl-indol-2-yl)-2-methyl-4-phenyl-3-butyn-1-ol ( 60.6 mg, 0.20 mmol) and toluene (1 mL), the reaction was complete at room temperature for 3 hours, concentrated, and flash column chromatography to obtain the product 9-ethyl-2-methyl-4-phenylcarbazole 51.3 mg, The yield was 90%. The product is solid, melting point 92-93 o C (ethyl acetate / n-hexane).

[0020] 1 H NMR (300 MHz, CDCl 3 ) δ 7.68-7.57 (m, 2H, ArH), 7.56-7.43 (m, 4H, ArH), 7.41-7.31 (m, 2H, ArH), 7.21 (s, 1H, ArH), 7.02-6.90 (m, 2H, ArH), 4.38 (q, J = 7.2 Hz, 2H, NCH 2 ), 2.59 (s, 3H, ArCH 3 ), 1.46 (t, J = 7.2 Hz, 3H, CH 3 ); 13 C NMR (75 MHz, CDCl 3 ) δ 141.4, 140.6, 140.1, 137.5, 135.5, 129.1, 128.3, 127.3, 124.9, 122.5, 122.1, 122.0, 118.3, 118.0, 108.1, 107.5, 37.3, 22.1, 13.7; IR (KBr) ν (cm -1 ) 3052, 3025, 2974, 2914, 2865, 1621, 1599, 1571, 1470, 1460, 1418, 1348, 1324, 1282, 1190, 1121, 1084, 1028; MS (70 ev, EI) m / z (%) 286 (M +...

Embodiment 2

[0022] According to the method described in Example 1, the difference is that the substrate and reagents used are: gold trichloride (3.5 mg, 0.012 mmol), 1-(1-ethyl-indol-2-yl)-2-methyl 3-hexyn-1-ol (51.1 mg, 0.20 mmol) and toluene (1 mL), then the reaction was complete at room temperature for 12 hours, concentrated, and flash column chromatography to obtain the product 2-methyl-4,9 -Diethyl-carbazole 38.3mg, the yield was 81%. The product is a colorless liquid.

[0023] 1 H NMR (300 MHz, CDCl 3 ) δ 8.18 (d, J = 8.1 Hz, 1H, ArH), 7.54-7.41 (m, 2H, ArH), 7.37-7.23 (m, 1H, ArH), 7.13 (s, 1H, ArH), 6.94 (s , 1H, ArH), 4.38 (q, J = 7.2 Hz, 2H, NCH 2 ), 3.29 (q, J = 7.5 Hz, 2H, ArCH 2 ), 2.61 (s, 3H, ArCH 3 ), 1.60-1.40 (m, 6H, 2×CH 3 ); 13 C NMR (75 MHz, CDCl 3 ) δ 140.6, 139.8, 139.4, 135.7, 124.4, 122.9, 122.3, 120.1, 118.6, 118.3, 108.1, 106.3, 37.3, 27.3, 22.2, 14.2, 13.7; IR (neat) ν (cm -1 ) 2970, 2943, 2877, 1618, 1599, 1570, 1468, 1458, 1432, 1374, ...

Embodiment 3

[0025] According to the method described in Example 1, the difference is that the substrate and reagents used are: gold trichloride (4.6 mg, 0.015 mmol), 1-(1-ethyl-indol-2-yl)-2-methyl Benzyl-3-octyne-1-ol (83.5 mg, 0.30 mmol) and toluene (2 mL), then the reaction was complete at room temperature for 19.5 hours, concentrated, and flash column chromatography to obtain the product 2-methyl-9-ethyl 57.8 mg of 4-butylcarbazole, the yield was 74%. The product is a colorless liquid.

[0026] 1 H NMR (300 MHz, CDCl 3 ) δ 8.08 (d, J = 7.8 Hz, 1H, ArH), 7.47-7.31 (m, 2H, ArH), 7.27-7.17 (m, 1H, ArH), 7.05 (s, 1H, ArH), 6.85 (s , 1H, ArH), 4.31 (q, J = 7.4 Hz, 2H, NCH 2 ), 3.26-3.07 (m, 2H, ArCH 2 ), 2.53 (s, 3H, ArCH 3 ), 1.88-1.75 (m, 2H, CH 2 ), 1.61-1.45 (m, 2H, CH 2 ), 1.40 (t, J = 7.4 Hz, 3H, ArCH 3 ), 0.99 (t, J = 7.4 Hz, 3H, CH 3 ); 13 C NMR (75 MHz, CDCl 3 ) δ 140.7, 139.9, 138.2, 135.5, 124.4, 123.0, 122.2, 121.2, 118.6, 118.5, 108.1, 106.3, 37.3...

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Abstract

The invention relates to a method for synthesising carbazole compounds, comprising the step of selectively reacting 1-(indol-2-yl)-3-alkyne-1-alcohol in the presence of gold trichloride in high region to synthesise functionalized carbazole. The method disclosed by the invention has the advantages that operation is simple, raw materials and reagents are available, conditions are moderate, the regioselectivity of the reaction is high, and the like; and moreover, a plurality of substituent groups can be introduced simultaneously, and the product is easily separated and purified. The method is suitable for synthesising various substituent carbazole compounds.

Description

Technical field [0001] The invention relates to a method for synthesizing functionalized carbazoles with high regioselectivity, that is, 1-(indol-2-yl)-3-yn-1-ol reacts to synthesize carbazoles under the catalysis of gold trichloride Class compound. [0002] Background technique [0003] Carbazole compounds widely exist in nature in many forms. Carbazole is also the basic skeleton of some drugs. Due to the superior and broad-spectrum biological activity of carbazole alkaloids, it has attracted great attention from medicinal chemists. The development of synthetically synthesized carbazole compounds with novel structures is very popular and has become an important new direction for the development of carbazole drugs. In recent years, the research and application of carbazole and its derivatives at home and abroad have been intensified, and the demand for carbazole has also increased dramatically. However, the literature on simple, fast and efficient synthesis of carbazole and its...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88
Inventor 麻生明仇友爱孔望清傅春玲
Owner ZHEJIANG UNIV