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A kind of preparation method of multi-substituted cycloheptatriene derivative

A technology for cycloheptatriene and derivatives, which is applied in the field of preparation of cycloheptatriene derivatives, can solve the problems of high risk of reaction substrates, long reaction time and the like, and achieves scientific and reasonable synthesis methods, simple synthesis methods, and high reaction efficiency. fast effect

Active Publication Date: 2021-05-14
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Obvious disadvantages of the above-mentioned process for the preparation of polysubstituted cycloheptatriene derivatives: longer reaction times, use of noble metals in the reaction, greater hazard of the reaction substrate

Method used

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  • A kind of preparation method of multi-substituted cycloheptatriene derivative
  • A kind of preparation method of multi-substituted cycloheptatriene derivative
  • A kind of preparation method of multi-substituted cycloheptatriene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1) Preparation of cycloheptatriene derivative 2a

[0022]

[0023] Add N-alkoxybenzamide 1a (0.2mmol, 55.9mg), iodobenzene diacetate (0.24mmol, 77.3mg) into a 25mL round bottom flask, add trifluoroethanol (4mL), stir at room temperature, and react 1 minute. After the reaction is complete, use a rotary evaporator to remove the solvent to obtain a crude product, which is separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1), and uses a rotary evaporator to remove the solvent to obtain the target The yield of the unsubstituted cycloheptatriene derivative 2a was 87%.

[0024] Spectral analysis data 2a:

[0025] 1 H NMR (500MHz, CDCl 3 )δ7.26(d,J=3.1Hz,1H),7.16(s,5H),6.50–6.42(m,3H),6.12–6.06(m,1H),5.06(t,J=4.3Hz,1H ), 4.25(qt,J=10.9,5.2Hz,2H),2.46–2.26(m,2H). 13 C NMR (125MHz, CDCl 3 )δ157.56, 142.91, 141.03, 133.64, 129.08, 128.64, 128.03, 127.73, 127.43, 127.13, 125.79, 125.35, 95.07, 69.25, 49.79, 22.59.

Embodiment 2

[0027] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0028]

[0029] Spectrum analysis data 2b:

[0030] 1 H NMR (500MHz, CDCl 3 )δ7.13(d, J=13.5Hz, 6H), 6.28(d, J=10.2Hz, 1H), 6.23(d, J=6.1Hz, 1H), 6.01(d, J=10.2Hz, 1H) ,4.99(t,J=4.2Hz,1H),4.23(qt,J=10.9,5.3Hz,2H),2.43–2.25(m,2H),1.88(s,3H). 13 C NMR (125MHz, CDCl 3 )δ157.96, 143.73, 143.08, 141.49, 130.80, 128.05, 127.74, 127.01, 126.29, 125.79, 125.61, 125.34, 94.76, 69.24, 49.38, 24.68, 22.59.

Embodiment 3

[0032] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0033]

[0034] Spectrum analysis data 2c:

[0035] 1 H NMR (500MHz, CDCl 3 )δ7.16(d, J=25.1Hz, 6H), 6.61(d, J=5.9Hz, 1H), 6.46(d, J=10.0Hz, 1H), 6.08(d, J=10.1Hz, 1H) ,5.04(s,1H),4.25(s,2H),2.47–2.23(m,2H). 13 CNMR (125MHz, CDCl 3 )δ157.13, 142.40, 140.36, 138.44, 130.05, 129.44, 128.74, 128.16, 127.61, 127.43, 125.58, 123.51, 95.72, 69.37, 49.57, 22.57.

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Abstract

The invention discloses a preparation method of multi-substituted cycloheptatriene derivatives, which belongs to the technical field of organic synthesis. The method is as follows: in the reactor, add substituted N-alkylbenzamide and iodobenzene diacetate. After the reaction was stirred in the solvent, the filtrate was concentrated using a rotary evaporator to obtain a crude product, which was separated by silica gel column chromatography to obtain the target compound. The synthesis method of the multi-substituted cycloheptatriene derivative provided by the invention has the characteristics of scientific rationality, simple synthesis method, high yield of the target compound, easy purification of the product, fast reaction, and room temperature reaction temperature. Its reaction equation is as follows:

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of cycloheptatriene derivatives. Background technique [0002] Cycloheptatriene derivatives widely exist in nature, and many drugs or drug intermediates contain cycloheptatriene derivatives as structural units. Most cycloheptatriene derivatives have biological activities such as antitumor, antibacterial, antiviral, anti-inflammatory, anti-ulcer, and insecticide. Since the 1990s, drugs based on cycloheptatriene derivatives and their structurally modified products Research is booming, and its structure types are increasing, and anti-tumor is a hot research field, and various types of structures have shown good anti-tumor activity. The structure of cycloheptatriene derivatives widely exists in many drugs, such as helical derivatives of penicillin, harringtonine, KT1-32 and so on. ((a) J. Am. Chem. Soc. 1998, 120, 8, 1914-1915 (b) J. Org. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 张林宝耿瑞森文丽荣任广义李明
Owner QINGDAO UNIV OF SCI & TECH
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