Seven-membered cyclopenta [b] indole derivative as well as synthesis method and application thereof

A synthetic method and a seven-membered ring technology, which can be applied in drug combination, bulk chemical production, organic chemistry, etc., can solve complex synthesis problems, and achieve the effects of easy-to-obtain raw materials, convenient operation, and strong biological activity

Active Publication Date: 2020-08-21
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Seven-membered ring compounds also have high biological activity, but the synt

Method used

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  • Seven-membered cyclopenta [b] indole derivative as well as synthesis method and application thereof
  • Seven-membered cyclopenta [b] indole derivative as well as synthesis method and application thereof
  • Seven-membered cyclopenta [b] indole derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1, the synthesis of b-1: 5-methyl-6-oxo-7-phenyl-6,8,9,10-tetrahydro-5H-[2,1-b]indole-8- Synthesis of Ethyl Carboxylate

[0063]

[0064] Alkyne ketone compounds, cyclopentanone ester compounds, accelerators, solvents, and additives are selected from 1-(1-methyl-1H-indol-2-yl)-3-phenylprop-2-yne-1- Ketone, ethyl 2-cyclopentanone carboxylate, Cs 2 CO 3 , dimethyl sulfoxide, and p-toluenesulfonic acid monohydrate, the amount of raw materials is 1-(1-methyl-1H-indol-2-yl)-3-phenylprop-2-yn-1-one 0.3 mmol, ethyl 2-cyclopentanone carboxylate 0.6mmol, Cs 2 CO 3 0.6mmol, solvent dimethyl sulfoxide 3mL, p-toluenesulfonic acid monohydrate 2.4mmol, react at 60°C for 2 hours, and react at 120°C for 2 hours to obtain the target product formula (b-1), yellow solid, isolated yield 99%.

[0065] NMR data: 1 H NMR (400MHz, CDCl 3 )δ1.18(t,J=6.8Hz,3H),2.28-2.37(m,1H),2.49-2.53(m,1H),2.65(brs,2H),3.75-3.88(m,4H),4.08 -4.13(m,2H),6.41-6.45(m,1H),7.21-7.41(m,8H),7.80-7....

Embodiment 2

[0067] Example 2, the synthesis of b-2: 3,5-dimethyl-6-oxo-7-phenyl-6,8,9,10-tetrahydro-5H-[2,1-b]indole -Synthesis of ethyl 8-carboxylate

[0068]

[0069] Alkyne ketone compounds, cyclopentanone ester compounds, accelerators, solvents, and additives are respectively selected from 1-(1,6-dimethyl-1H-indol-2-yl)-3-phenylprop-2-yne -1-keto, ethyl 2-cyclopentanone carboxylate, Cs 2 CO 3 , dimethyl sulfoxide, and p-toluenesulfonic acid monohydrate, the amount of raw materials is 1-(1,6-dimethyl-1H-indol-2-yl)-3-phenylprop-2-yne-1 - Ketone 0.3mmol, 2-cyclopentanone ethyl carboxylate 0.6mmol, Cs 2 CO 3 0.6mmol, solvent dimethyl sulfoxide 3mL, p-toluenesulfonic acid monohydrate 2.4mmol, react at 60°C for 2 hours, and react at 120°C for 2 hours to obtain the target product formula (b-2), yellow solid, isolated yield 99%.

[0070] NMR data: 1 H NMR (400MHz, CDCl 3 )δ1.18(t,J=7.2Hz,3H),2.28-2.37(m,1H),2.50(brs,4H),2.62-2.68(m,2H),3.78(s,3H),3.85-3.88 (m,1H),4.05-4.16(m,2H),...

Embodiment 3

[0072] Example 3, the synthesis of b-3: 5-methyl-6-oxo-7-(p-tolyl)-6,8,9,10-tetrahydro-5H-[2,1-b]indole -Synthesis of ethyl 8-carboxylate

[0073]

[0074] Alkyne ketone compounds, cyclopentanone ester compounds, accelerators, solvents, and additives are respectively selected from 1-(1-methyl-1H-indol-2-yl)-3-(p-tolyl)prop-2-yne -1-keto, ethyl 2-cyclopentanone carboxylate, Cs 2 CO 3 , dimethyl sulfoxide, and p-toluenesulfonic acid monohydrate, the amount of raw materials is 1-(1-methyl-1H-indol-2-yl)-3-(p-tolyl)prop-2-yne-1 - Ketone 0.3mmol, 2-cyclopentanone ethyl carboxylate 0.6mmol, Cs 2 CO 3 0.6mmol, solvent dimethyl sulfoxide 3mL, p-toluenesulfonic acid monohydrate 2.4mmol, react at 60°C for 2 hours, and react at 120°C for 2 hours to obtain the target product formula (b-3), yellow solid, isolated yield 93%.

[0075] 1 H NMR (400MHz, CDCl 3 )δ1.89(t,J=6.8Hz,3H),2.27-2.36(m,1H),2.37(s,3H),2.44-2.53(m,1H),2.63-2.66(m,2H),3.83 (s,3H),3.86-3.88(m,1H),4.05-4.16(m,2H)...

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Abstract

The invention discloses a synthesis method of a seven-membered cyclopenta [b] indole derivative, which is characterized in that an acetylenic ketone compound and a cyclohexanone ester compound are used as raw materials, and the seven-membered cyclopenta [b] indole derivative shown as a formula (b) (See the specification) is synthesized by adopting a 'one-pot method'. The synthesis method specifically comprises the following steps: step 1, promoting C-C bond insertion through alkali to realize an expansion reaction so as to obtain a seven-membered ring compound, and step 2, carrying out a nucleophilic addition reaction under the action of p-toluenesulfonic acid. The preparation method provided by the invention has the advantages of simple and easily available raw materials, good universality, simple and convenient post-treatment, good yield, environmental friendliness and the like. The invention also provides an application of the seven-membered ring cyclopenta [b] indole derivative shown in the formula (b) in medicines.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and specifically relates to seven-membered cyclopenta[b]indole derivatives and their synthesis methods and applications. Background technique [0002] Cyclopenta[b]indole compounds are an important class of organic compounds, which are the main structural units in many natural products and drugs, and most of them have strong biological activities. It can be used as an intermediate in organic synthesis and has great value in drug synthesis. Therefore, people have paid a lot of attention to the synthesis research of cyclopenta[b]indole compounds. At present, there are many reports on the synthesis methods of such compounds, and great progress has been made. For example, under the action of silver and polyphosphoric acid, cyclopenta[b]indole derivatives can be obtained. Seven-membered ring compounds also have high biological activity, but the synthesis is complex and generally requires t...

Claims

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Application Information

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IPC IPC(8): C07D209/94A61P35/00
CPCC07D209/94A61P35/00Y02P20/55
Inventor 李艳忠王孟丹尹利强杨亚婕宋博徐穆榕穆远洋王野袁洋冯烨
Owner EAST CHINA NORMAL UNIVERSITY
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