Synthetic method of indanone by gold-catalysis

A synthesis method and a gold catalyst technology, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of low yield, few reports on indanone synthesis, long reaction time, etc., and achieve high Reaction yield, wide range of reaction applications, simple and convenient reaction operation

Inactive Publication Date: 2015-02-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, although the structure of indanone plays a very important role in many aspects, there are very few reports

Method used

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  • Synthetic method of indanone by gold-catalysis
  • Synthetic method of indanone by gold-catalysis
  • Synthetic method of indanone by gold-catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Substrate 1 (1mmol) and Ph 3 wxya 2(0.05mmol, 36.9mg) in dry toluene (2mL) was placed in a round-bottomed flask with a rubber stopper, oxygen was continuously fed in and slowly discharged out of the bottle, and reacted at 80°C for 9h. After the reaction is finished, use petroleum ether / ethyl acetate (v / v=100 / 1) as the eluent system, and use 200-300 mesh silica gel as the stationary phase to perform column chromatography separation to finally obtain the target compound I. The reaction yield 75%. Its reaction equation is:

[0034]

[0035] The spectral data of product I is: HRMS (ESI): m / z: [M+H] + 269.0388; 1 H NMR (600MHz, CDCl 3 )δ=10.30(s,1H),7.98(d,J=7.4Hz,1H),7.63(d,J=7.2Hz,1H),7.52–7.45(m,5H),7.34(t,J=7.4 Hz, 1H).

Embodiment 2

[0037] Change the reaction substrate 1 to the reaction substrate 2, change the elution system to petroleum ether / ethyl acetate (v / v=50 / 1), and the others are the same as in Example 1 to obtain the target compound II with a reaction yield of 82%. . Its reaction equation is:

[0038]

[0039] The spectral data of product I is: HRMS (ESI): m / z: [M+H] + 279.1016; 1 H NMR (600MHz, CDCl 3 )δ=10.27(s,1H),7.82(d,J=7.5Hz,1H),7.52(d,J=8.6Hz,2H),7.42(s,1H),7.25(d,J=7.5Hz, 1H), 7.02(d, J=8.6Hz, 2H), 3.88(s, 3H), 2.37(s, 3H).

Embodiment 3

[0041] Change the reaction substrate 1 to the reaction substrate 3, change the elution system to petroleum ether / ethyl acetate (v / v=5 / 1), and the others are the same as in Example 1 to obtain the target compound III with a reaction yield of 82%. . Its reaction equation is:

[0042]

[0043] The spectral data of product I is: HRMS (ESI): m / z: [M+H] + 317.0777; 1 H NMR (600MHz, CDCl 3 )δ=10.25(s,1H),7.57(m,2H),7.55(d,J=8.7Hz,2H),7.03(d,J=8.7Hz,2H),6.70(dd,J=8.2Hz, 2.2Hz, 1H), 3.91(s, 3H), 3.89(s, 3H).

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Abstract

The invention provides a synthetic method of indanone. The general equation of reaction is defined in the specification. Reaction substrates of the method are different substituted 1,5-eneyne. A catalyst is Ph3PAuCl, Ph3PAuNTf2, HAuCl4, NaAuCl4, Ph3PAuOTf, Ph3PAuSbF6 or IPrAuCl. A medium required by the reaction is methanol, toluene, dichloromethane, 1,2-dichloroethane, chloroform or tetrahydrofuran. The reaction is implemented by microwave heating which promotes the reaction, and also can be implemented by heating and stirring. According to the reaction, cyclization and oxidation can be cascaded in the presence of a gold catalyst to generate a series of indanone-containing compounds. The method provided by the invention has characteristics of simple operation, wide range of application, few by-products, high yield and green reaction.

Description

(1) Technical field [0001] The invention relates to a synthetic method of indanone. Specifically, it relates to a method for generating indanone through cyclization oxidation of 1,5-enyne with specific substitution in the presence of a gold catalyst. (2) Background technology [0002] Indanone structures widely exist in natural products, synthetic drugs, pesticides, dyes, amino color development and various fine chemicals, and have a wide range of uses. This kind of compound is also an important intermediate in the research of synthetic chemistry. It has many reaction sites and strong reactivity, and can be used in the synthesis of compounds with various structural types and different uses. Research on it not only has important academic value, but also has broad Application prospect. (Chin.J.Org.Chem.2010,30,988–996.) At present, there are more than 100 naturally occurring indanone compounds, such as Donepezil, mukagolactone, Indacrinone, MJ-II-38, Isoprekinamycin and Pau...

Claims

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Application Information

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IPC IPC(8): C07C49/757C07C45/51
CPCC07C45/513C07C2602/08C07C49/757
Inventor 刘永祥程卯生彭肖石郭佳刘洋
Owner SHENYANG PHARMA UNIVERSITY
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