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Method for synthesizing C3-carbonyl acetylindole derivatives

A technology of carboacetyl indole derivatives and synthesis methods, which is applied in the field of synthesis of C3-carboacetoyl indole derivatives, can solve the problems of cumbersome technology and low yield, and achieve simple and easy-to-obtain raw materials, easy products, and simple steps Effect

Active Publication Date: 2019-01-18
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] In order to overcome the deficiencies that the prior art is loaded down with trivial details and productive rate is low, the object of the present invention is to provide a kind of simple and efficient C3-carboacetylindole derivative synthetic method, the raw material used in this method is cheap and easy to get and nontoxic, The whole operation process is simple and easy

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  • Method for synthesizing C3-carbonyl acetylindole derivatives
  • Method for synthesizing C3-carbonyl acetylindole derivatives
  • Method for synthesizing C3-carbonyl acetylindole derivatives

Examples

Experimental program
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Embodiment 1

[0039] The synthetic method of C3-carboacetoindole derivative, comprises the following steps:

[0040] (1) Add N-methylindole (26.2mg, 0.2mmol), α-diazo-β-ketoester (54.5mg, 0.25mmol), zinc acetate catalyst (7.28mg, 0.04mmol) in a sealed tube , anhydrous 1,2-dichloroethane 1mL, the mixture was stirred and reacted at 120°C for 12h, then stopped heating, cooled to room temperature, spin-dried, and further separated and purified by column chromatography to obtain 54.6mg of the product with a yield of : 85%.

[0041] The structural characterization data of the product obtained in this embodiment are as follows:

[0042] 1 H NMR (400MHz, CDCl 3 )δ8.36–8.31(m,1H),7.58(s,1H),7.42(d,J=7.4Hz,2H),7.28–7.16(m,6H),5.31(s,1H),4.15(q , J=7.1Hz, 2H), 3.67(s, 3H), 1.17(t, J=7.1Hz, 3H). figure 1 .

[0043] 13 C NMR (101MHz, CDCl 3 )δ187.4, 169.1, 137.4, 136.1, 134.4, 129.4, 128.6, 127.8, 126.7, 123.7, 122.9, 122.8, 115.2, 109.6, 62.1, 61.6, 33.6, 14.1. figure 2 .

[0044] GC-MS(ESI):m...

Embodiment 2

[0048] The synthetic method of C3-carboacetoindole derivative, comprises the following steps:

[0049] (1) Add N-phenylindole (38.6mg, 0.2mmol), α-diazo-β-ketoester (54.5mg, 0.25mmol), zinc acetate catalyst (7.28mg, 0.04mmol) in a sealed tube , anhydrous 1,2-dichloroethane 1mL, the mixture was stirred and reacted at 120°C for 12h, then stopped heating, cooled to room temperature, spin-dried, and further separated and purified by column chromatography to obtain 66.6mg of the product with a yield of : 87%.

[0050] The structural characterization data of the product obtained in this embodiment are as follows:

[0051] 1 H NMR (400MHz, CDCl 3 )δ8.42(d,J=7.8Hz,1H),7.83(s,1H),7.51–7.42(m,4H),7.38 (dt,J=15.9,7.8Hz,4H),7.30–7.19(m ,5H), 5.37(s,1H), 4.17(q, J=7.1Hz, 2H), 1.19(t, J=7.1Hz, 3H). image 3 .

[0052] 13 C NMR (101MHz, CDCl 3 )δ187.9, 169.0, 138.1, 137.0, 134.9, 134.1, 129.9, 129.4, 128.6, 128.2, 127.9, 127.0, 125.0, 124.3, 123.4, 123.0, 116.9, 110.8, 62.2, 61.6, 14...

Embodiment 3

[0058] The synthetic method of C3-carboacetoindole derivative, comprises the following steps:

[0059] (1) Add N-methylindole (26.2 mg, 0.2 mmol), p-methoxy-α-diazo-β-ketoester (62,0 mg, 0.25 mmol), zinc acetate catalyst in a sealed tube (7.28mg, 0.04mmol), anhydrous 1,2-dichloroethane 1mL, the mixture was stirred and reacted at 120°C for 12h, then stopped heating, cooled to room temperature, spin-dried, and further separated and purified by column chromatography to obtain Product 49.1 mg, yield: 70%.

[0060] The structural characterization data of the product obtained in this embodiment are as follows:

[0061] 1 H NMR (400MHz, CDCl 3 )δ8.32(dd,J=6.1,2.6Hz,1H),7.57(s,1H),7.33(d,J=8.6Hz,2H),7.22–7.14(m,3H),6.78(d,J =8.6Hz, 2H), 5.25(s, 1H), 4.14(q, J=7.1Hz, 2H), 3.65(d, J=6.7Hz, 6H), 1.16(t, J=7.1Hz, 3H). See the hydrogen spectrum Figure 5 .

[0062] 13 C NMR (101MHz, CDCl 3 )δ187.8, 169.5, 159.2, 137.3, 136.1, 130.5, 126.7, 126.6, 123.7, 122.9, 122.7, 115.1, 114.1,...

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Abstract

The invention discloses a method for synthesizing C3-carbonyl acetylindole derivatives. The method comprises the following steps: adding an N-substituted indole compound, a diazo compound, a catalystand an organic solvent into an airtight seal tube, reacting at a temperature of 120 DEG C for 12 hours, and producing the C3-carbonyl acetylindole derivatives. The molar ratio of the N-substituted indole compound to diazo is 1:1.25, and the ratio of the catalyst is 2-%. The method disclosed by the invention is simple and high-efficiency, the used raw materials are cheap, readily available and non-toxic, and the preparation method is insensitive to air and water. In addition, the whole experimental operation process is simple and feasible, the steps are simple and convenient, and the product iseasy to purify.

Description

technical field [0001] The invention relates to the field of synthesis of indole derivatives, in particular to a synthesis method of C3-carboacetyl indole derivatives. Background technique [0002] Indole compounds are important skeletons of many natural products and drug molecules, and the development of their efficient preparation reactions is one of the research fields of organic synthetic chemistry that has attracted much attention. Among them, functional acylated indole can be easily transformed into heterocyclic compounds with structural diversity through chemical synthesis, and how to quickly construct functional acylated indole has attracted much attention in recent years. [0003] The synthesis methods of simple 3-acylindole derivatives reported so far mainly include: one is to obtain 3-acylated products through Friedel-Crafts acylation reaction using indole as a nucleophile and various acylating reagents. Such as (1) acid chlorides are used as acylating reagents, ...

Claims

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Application Information

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IPC IPC(8): C07D209/24C07D209/12
CPCC07D209/12C07D209/24
Inventor 曾伟胡新伟
Owner SOUTH CHINA UNIV OF TECH