Synthetic method of alkenyl indole derivative

A technology of alkenyl indole derivatives and synthesis methods, which is applied in the field of synthesis of alkenyl indole derivatives, and can solve problems such as environmental hazards and low atom economy

Pending Publication Date: 2022-02-25
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The disadvantage of this method is that the reaction substrate is limited, expensive transition metal catalysts are required, and there is potential harm to the environment. At the same time, decarboxylation is required during the reaction process, and the atom economy is low.

Method used

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  • Synthetic method of alkenyl indole derivative
  • Synthetic method of alkenyl indole derivative
  • Synthetic method of alkenyl indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Implementation 1: The reaction steps of the method for preparing (E)-3-(2-(2-methyl-1,3-dithian-2-yl)vinyl)-1H-indole:

[0022] In a 25 mL round bottom flask, add methyl-β-chloro-ethylene-1,3-dithiane (39 mg, 0.2 mmol) and indole (29 mg, 0.25 mmol), and dissolve with 6 mL of 1,2-dichloro After dissolving ethane, add indium tribromide (10.6mg, 0.03mmol) and indium tribromide (6.63mg, 0.03mmol), stir the reaction at room temperature, stop the reaction after TLC detects that the reaction is complete, and the mixture is washed with 1NNaHCO 3 (10 mL) and extracted with EtOAc (15 mL), the organic layer was separated and the aqueous phase was re-extracted with EtOAc (15x3 mL), the combined organic extracts were washed with brine (15x3 mL) and washed in anhydrous Na 2 SO 4 The product was obtained by column chromatography after evaporation of the solvent (yield 82%).

Embodiment 1

[0023] The structure and NMR data of the product (E)-3-(2-(2-methyl-1,3-dithian-2-yl)vinyl)-1H-indole obtained in Example 1 are as follows:

[0024]

[0025] 1 H NMR (400MHz, Chloroform-d) δ8.16(s, 1H), 7.90(d, J=7.0Hz, 1H), 7.37(d, J=7.5Hz, 1H), 7.27(d, J=2.6Hz ,1H),7.27–7.17(m,2H),7.00(d,J=15.9Hz,1H),6.35(d,J=15.9Hz,1H),3.05–2.94(m,2H),2.84–2.72( m,2H),2.07–1.98(m,1H),1.97–1.86(m,1H),1.75(s,3H). 13 C NMR (101MHz, CDCl 3 )δ136.88, 130.73, 125.60, 124.34, 123.85, 122.75, 120.54, 120.26, 114.38, 111.49, 50.98, 30.11, 27.79, 25.06.

Embodiment 2

[0026] Implementation 2: the reaction steps of the method for preparing (E)-2-(2-(2-(tert-butyI)-1,3-dithian-2-yl)vinyl)-3-methyl-1H-indole:

[0027] In a 25ml round bottom flask, add phenyl-β-chloro-ethylene-1,3-dithiane (47mg, 0.2mmol) and 3-methylindole (52.4mg, 0.4mmol) Add indium trichloride (8.8mg, 0.03mmol) after the methyl chloride dissolves, stir the reaction at 50°C, stop the reaction after the reaction is complete as detected by TLC, and wash the mixture with 1N NaHCO 3 (10 mL) and extracted with EtOAc (15 mL), the organic layer was separated and the aqueous phase was re-extracted with EtOAc (15x3 mL), the combined organic extracts were washed with brine (15x3 mL) and washed in anhydrous Na 2 SO 4 The product was obtained by column chromatography after evaporation of the solvent (yield 80%).

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Abstract

The invention belongs to the field of organic synthesis, and relates to a synthetic method of alkenyl indole derivatives. The alkenyl indole compound has important research value in the aspects of synthesis and pharmaceutical activity, but conventional synthesis steps are tedious, conditions are harsh, and use of expensive heavy metals and positioning groups is involved. The invention provides a synthetic method of the alkenyl indole derivative, which comprises the following steps: by taking an alkenyl-1, 3-dithiane derivative and substituted indole as raw materials, synthesizing the alkenyl indole derivative through migration of a thiane ring under the action of a catalyst. The method is an efficient and simple synthesis method, has the advantages of mild reaction, high efficiency, simplicity in operation and economical raw materials, and has very high practicability.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a synthesis method of a class of alkenylindole derivatives. Background technique [0002] Alkenylindole compounds have important pharmacological activities, such as antitumor effect (J.Med.Chem.,55,1940-1956,), anti-inflammatory effect, antifungal effect (Journal of Pharmacy, 5,459-462), antimalarial Effect (J.Med.Chem., 56, 6200-6215) and so on. In addition, alkenylindole derivatives are important intermediates in organic synthesis. Due to the unsaturated double bond structure in the alkenylindole derivatives, they can not only construct different tetrahydrocarbazole structures through Diels-Alder reactions with different dienophiles, but also undergo Pauson-Khand reactions and Cross-metathesis of alkenes and many other reactions. At present, there are few studies on the structure of alkenylindole containing thiane ring, and there are few reports. [0003] At present, the main ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06C07D471/06C07J43/00C07K5/062
CPCC07D409/06C07D471/06C07J43/003C07K5/06026C07B2200/07
Inventor 唐寿初董康
Owner LANZHOU UNIVERSITY
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