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Method for synthesizing 3-substituted indole and 2,3-disubstituted indole

A technology of indole and C7-C12, applied in the field of alkaloids, can solve the problems of low yield and achieve the effects of simple raw materials, shortened reaction time and high reactivity

Inactive Publication Date: 2013-06-05
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

[0003] Since most of the reactions of indoles and imines catalyzed by Lewis acids and Bronsted acids inevitably generate bisindole products, resulting in low yields of the target products 3-substituted indole and 2,3-disubstituted indole

Method used

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  • Method for synthesizing 3-substituted indole and 2,3-disubstituted indole
  • Method for synthesizing 3-substituted indole and 2,3-disubstituted indole
  • Method for synthesizing 3-substituted indole and 2,3-disubstituted indole

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Experimental program
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Embodiment 1

[0027] Embodiment 1: the synthesis of compound (1a)

[0028]

[0029] In a nitrogen-protected reaction flask, 2-methylindole (1.0 mmol) was added, followed by 4 ml of dry dichloromethane. After cooling to 0°C, elemental iodine (0.1 mmol) was added. After stirring and dissolving, imine (1.0 mmol) was added to the system. After constant temperature reaction for 5 min, saturated sodium thiosulfate solution was added to quench the reaction. After static separation, the aqueous layer was extracted three times with dichloromethane (3×3 mL). After combining the organic layers, they were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product compound 1 was obtained by silica gel column chromatography.

[0030] 4-Methyl-N-((2-methyl-1H-indol-3-yl)(phenyl)methyl)benzenesulfonamide (1a). Yield: 90%, white solid, 1 H NMR (400MHz, CDCl 3 )δ7.70(s, 1H), 7.46(d, J=8.0Hz, 2H), 7.39(d, J=7.4Hz, 2H), 7.29-7.11(m, 4H), 7.03(m, 4H), 6.88(t, J...

Embodiment 2

[0031] Embodiment 2: the synthesis of compound (1b)

[0032]

[0033] In a nitrogen-protected reaction flask, 2,7-dimethylindole (1.0 mmol) was added, followed by 4 ml of dry dichloromethane. After cooling to 0°C, elemental iodine (0.1 mmol) was added. After stirring and dissolving, imine (1.0 mmol) was added to the system. After constant temperature reaction for 5 min, saturated sodium thiosulfate solution was added to quench the reaction. The layers were separated, and the aqueous layer was extracted three times (3×3 mL). After combining the organic layers, they were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product compound was obtained by silica gel column chromatography.

[0034] N-((2,7-Dimethyl-1H-indol-3-yl)(phenyl)methyl)-4-methylbenzonesulfonamide (1g). Yield 99%, white solid, melting point: 144-145°C; 1 H NMR (400MHz, d 6 -Acetone) δ9.74(s, 1H), 7.50(d, J=7.9Hz, 2H), 7.42(d, J=7.6Hz, 2H), 7.24(t, J=7.4Hz, 2H...

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Abstract

The invention provides a method for synthesizing 3-substituted indole and 2,3-disubstituted indole. Various substituted 3-substituted indole and 2,3-disubstituted indole can be obtained by reacting simple indole or 2-substituted indole with imine under the catalysis of iodine. The method is simple and practical, and has easily available raw materials and high yield. The reaction product can be conveniently subjected to subsequent conversion.

Description

technical field [0001] The invention relates to alkaloids containing indole rings, in particular to a method for synthesizing 3-substituted indole and 2,3-disubstituted indole. Background technique [0002] Alkaloids containing indole rings are widely found in nature and account for a considerable proportion of isolated and identified natural products. Most of the indole alkaloids show important biological activities. Among the more than 3,000 known natural indole alkaloids, more than 40 are therapeutic drugs [Document 1: Austin J., MacMillan C.J.Am.Chem.Soc ., 2002, 124, 172. Literature 2: Li Jitai, Dai Hongguang, Lin Zhiping. Progress in Chemistry, 2007, 19, 751.]. For example, it can treat various diseases such as cardiovascular disease, diabetes and lung cancer [Document 3: Shi Lei, Wang Xinping, Cai Tianxi. Organic Chemistry, 2001, 21, 200.], and indole ring compounds can be used to synthesize dyes, prepare spices, Used as plant auxin, feed additive [Document 4: Barri...

Claims

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Application Information

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IPC IPC(8): C07D209/14C07D209/08
Inventor 周永贵段英陈木旺陈庆安
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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