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Method for regioselectively synthesizing indene-indole derivative

A technology of regioselectivity and indole derivatives, applied in organic chemistry and other fields, can solve problems such as difficult to control the use of regioselective oxidant stoichiometry

Pending Publication Date: 2022-02-08
LANZHOU UNIVERSITY
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Problems solved by technology

In addition, the C3 position of indole is the most active position for electrophilic substitution reactions, but the functionalization of the C2 position requires the assistance of a directing group, and requires relatively expensive noble metal catalysts such as rhodium, ruthenium, and palladium to achieve
The reported synthetic methods still face certain limitations, including difficult-to-control regioselectivity, use of oxidant stoichiometry, etc. (Angew.Chem.,Int.Ed.2015,54,11956.)

Method used

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  • Method for regioselectively synthesizing indene-indole derivative
  • Method for regioselectively synthesizing indene-indole derivative
  • Method for regioselectively synthesizing indene-indole derivative

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[0014] The present invention will be further described in detail below in conjunction with specific examples, which are only used to explain the present invention, and are not intended to limit the scope of the present invention. Unless otherwise specified, the test methods used in the following examples are conventional methods: the materials and reagents used, unless otherwise specified, are commercially available reagents and materials.

[0015] The product structure of the example of concrete implementation is as follows:

[0016]

[0017] The synthetic process of 3,4,5-trimethoxyphenylindene-indole compounds is as follows:

[0018]

[0019] The specific steps are as follows: in a 10 ml round bottom flask, add indole compounds (0.25mmol) and 3,4,5-trimethoxyphenyl-β-chloro-ethylene-1,3-dithiane (69mg, 0.2mmol), add catalyst indium (Ⅲ) (0.03mmol) after dissolving with 6 milliliters of solvents, stir the reaction at room temperature for 24-48h, TLC detects until the r...

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Abstract

The invention discloses a method for regioselectively synthesizing an indene-indole derivative. An indole compound and electron-rich aryl alkenyl-1, 3-dithiane are used as raw materials, and under the action of Lewis acid, an oxidizing agent or protonic acid, the indene-indole derivative is synthesized through one-step reaction with high regioselectivity and high yield. The method has the advantages of good selectivity, mild reaction conditions, high yield, simplicity and safety in operation and the like. The indene-indole derivative and the related indanone structure synthesized by the invention are important structural fragments of complex indole natural products and active pharmaceutical molecules, and meanwhile, the method for regioselectively synthesizing the indene-indole derivative can be used for preparing related pharmaceutical and chemical intermediates, and has wide application prospects in the field of pharmaceutical chemistry.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for selectively synthesizing indene-indole derivatives from indole C2 and C3 regions. . Background technique [0002] Substituted indene and its related indenone derivatives are important structural units in many natural products, such as acetylcholinease inhibitor donepezil, endothelin receptor antagonist enrasentan, anti-inflammatory sulindac, aldosterone synthase inhibitor and anti-tuberculosis drugs, etc. Indene and indenone derivatives are also key intermediates in drug synthesis, natural products and other bioactive compounds (Eur J Med Chem 138,182-198(2017).). Indene-indole derivatives exist in natural products and a variety of biologically active drugs, and it is critical to find a method for synthesizing indene-indole derivatives regioselectively at C2 and C3 of indole. In addition, the C3 position of indole is the most active position for electro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C07D491/056
CPCC07D409/04C07D491/056
Inventor 唐寿初李嘉
Owner LANZHOU UNIVERSITY
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