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Preparation method of polysubstitution dihydropyrimidine indolone derivative

A technology of dihydropyrimidine and indolinone, which is applied in the field of preparation of dihydropyrimidoindolinone derivatives, achieves the effects of high yield, scientific and reasonable synthesis method, and easy purification of products

Active Publication Date: 2018-11-02
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 dihydropyrimidoindolinone derivatives: the use of the noble metal rhodium

Method used

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  • Preparation method of polysubstitution dihydropyrimidine indolone derivative
  • Preparation method of polysubstitution dihydropyrimidine indolone derivative
  • Preparation method of polysubstitution dihydropyrimidine indolone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) Preparation of dihydropyrimidoindolinone derivative 3aa

[0023]

[0024] Add N-methoxyindolecarboxamide 1a (0.2mmol, 38.0mg), 2a (0.4mmol, 41.7mg) and cobalt acetate (0.02mmol, 5.0mg), silver acetate (0.4mmol, 5.0mg) to 15ml thick wall pressure tube mmol, 66.8mg), sodium acetate (0.4mmol, 54.4mg) and tricyclohexylphosphine (0.04mmol, 11.2mg) were added to hexafluoroisopropanol (2mL), stirred in an oil bath at 120°C, and reacted for 3 hours. After the reaction, the solvent was removed using a rotary evaporator to obtain the crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate = 8 / 1), and the solvent was removed using a rotary evaporator to obtain the target The product is unsubstituted dihydropyrimidoindolinone 3aa, and its yield is 95%.

[0025] Spectral analysis data 3aa:

[0026] 1 H NMR(500MHz, CDCl 3 )δ8.45(d,J=8.3Hz,1H),7.46-7.29 (m,7H),7.22(t,J=7.5Hz,1H),6.07(s,1H),4.57(dd,J=9.8 ,5.4Hz, 1H...

Embodiment 2

[0028] Use 1b instead of 1a in Example 1, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0029] Spectral analysis data 3ba:

[0030]

[0031] 1 H NMR(500MHz, CDCl 3 )δ8.39(dd,J=9.0,4.7Hz,1H), 7.40 (dt,J=11.6,6.7Hz,3H), 7.33(d,J=6.8Hz,2H), 7.08(dd,J=8.8 ,2.3 Hz,1H),7.04(td,J=9.2,2.4Hz,1H),6.03(s,1H),4.57(dd,J=9.6, 5.5Hz,1H),3.98–3.87(m,2H) , 3.85(s, 3H). 13 C NMR(125MHz, CDCl 3 )δ160.4, 158.5, 152.3, 138.9, 138.0, 131.8, 130.4, 130.4, 129.0, 1228.2, 116.4, 116.4, 112.1, 111.9, 105.9, 105.7, 104.9, 62.8, 54.6, 40.9.

Embodiment 3

[0033] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0034]

[0035] Spectral analysis data 3ca:

[0036] 1 H NMR(500MHz, CDCl 3 )δ8.36(d,J=8.8Hz,1H),7.46-7.33 (m,5H),7.34-7.30(m,3H),7.29-7.23(m,2H),6.00(s,5H),4.56 (dd, J=9.1,5.6Hz,1H), 3.98–3.85(m,2H), 3.85(s,3H). 13 C NMR(125 MHz, CDCl 3 )δ152.1, 138.7, 137.9, 133.8, 130.7, 129.0, 128.7, 128.2, 124.4, 119.8, 116.4, 104.4, 62.8, 54.5, 40.9.

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Abstract

The invention discloses a preparation method of a novel polysubstitution dihydropyrimidine indolone derivative, which belongs to the technical field of organic synthesis. The preparation method comprises the following steps: adding substitution N-methoxyindolamide into a reactor, substituting styrene, cobaltous acetate, silver acetate, sodium acetate, 4-methylpyridine and tricyclohexylphosphine, stirring in a solvent, after the reaction is finished, concentrating filtrate by using a rotary evaporator to obtain a crude product, separating the crude product by virtue of silica gel column chromatography to obtain a target compound. The synthetic method of the polysubstitution dihydropyrimidine indolone derivative provided by the invention has the characteristics of science, reasonability, simple synthetic method, high yield of target compounds, ease in purifying the product and the like. A reaction equation is shown in the description.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a dihydropyrimidoindolinone derivative. Background technique [0002] Nitrogen-containing heterocycles are widely present in natural products and molecules with biological and medical activities. Among these heterocyclic compounds, pyrimidinone and indole are two important types of nuclei. Pyrimidone compounds have good application prospects in many fields, for example, anti-cancer and antibacterial activities. (J. Med. Chem. 1987, 30, 1256-1261.) Indole compounds also play an indispensable role in drug design and the synthesis of natural products. For example, compounds with indole as the core are used for hypertension treatment and antibacterial drugs, respectively. ((a)Hypertension.1997,29,651-658.(b)J.Antimicrob.Chemother.2004,54,549-552.) [0003] As a combination of two nitrogen-containing heterocycles of pyrimidinone and indole, d...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 张林宝朱明辉文丽荣李明
Owner QINGDAO UNIV OF SCI & TECH
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