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A kind of preparation method of 4h-chromene derivative

A technology of derivatives and chromenes, applied in the field of organic synthesis, can solve the problems of high price and complex preparation and operation of transition metal catalysts, and achieve the effects of scientific and reasonable synthesis methods, simple experimental operations, and simple synthetic routes

Active Publication Date: 2020-04-10
QINGDAO UNIV OF SCI & TECH
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Using the above method to prepare 4H-derivatives in the laboratory has obvious disadvantages: 1) It is necessary to select an expensive transition metal catalyst or use a Lewis acid; 2) the preparation of the transition metal catalyst is complicated;

Method used

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  • A kind of preparation method of 4h-chromene derivative
  • A kind of preparation method of 4h-chromene derivative
  • A kind of preparation method of 4h-chromene derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0025] 1) Preparation of 4H-chromene derivative 3a

[0026]

[0027] Add thioamide 1a (0.5mmol, 127.7mg), p-methylenebenzoquinone 2a (0.6mmol, 186.3mg) and NEt into a 25mL single-necked flask 3 (0.25mmol, 25.3mg). Add ethanol (5 mL), stir in an oil bath at 70° C., and react for 10 hours. After the reaction was completed, cool to room temperature, remove the solvent with a rotary evaporator, and the residue was separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=50 / 1), and the obtained solid 4H-color The yield of ene derivative 3a was 85%.

[0028] Spectral analysis data 3a:

[0029] 1 H NMR(d-DMSO,500MHz)δ1.22(s,18H,CH3),4.95(s,1H,CH),6.57(s,2H,ArH),6.74(s,1H,-OH,missing after deuteriation ),7.15(t,J=7.7Hz,1H,ArH),7.17-7.22(m,3H,ArH),7.25-7.28(m,3H,ArH),7.34-7.37(m,2H,ArH),7.41 -7.43(m,5H,ArH),12.73(s,1H,NH,missing after deuteriation). 13 C NMR (d-DMSO, 125MHz) δ194.1, 159.5, 152.2, 148.6, 141.3, 139.4, 138.1, 137.4, 129.8, 129...

Embodiment 2

[0031] Replace 2a in Example 1 with 2b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0032]

[0033] Spectrum analysis data 3b:

[0034] 1 H NMR (CDCl 3 ,500MHz)δ1.30(s,18H,t-Bu),4.88(s,1H,CH),5.02(s,1H,OH),6.54(s,2H,ArH),7.01(d,J=8.6 Hz,1H,ArH),7.17-7.22(m,3H,ArH),7.25(s,1H,ArH),7.29-7.31(m,1H,ArH),7.35(t,J=7.3Hz,2H,ArH ),7.39-7.46(m,5H,ArH),13.20(s,1H,NH). 13 CNMR (CDCl 3 ,125MHz)δ194.4,159.6,152.2,147.7,141.2,137.1,136.9,135.7,131.7,130.3,129.6,129.1,129.0,128.1,126.4,124.7,123.4,122.5,117.9,04,117.6 .HRMS(ESI)m / z calcd for C 36 h 36 NO 3 BrNa + [M+Na] + 632.1776,found,632.1774.

Embodiment 3

[0036] Replace 2a in Example 1 with 2c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0037]

[0038] Spectrum analysis data 3c:

[0039] 1 H NMR (CDCl 3 ,500MHz)δ1.29(s,18H,t-Bu),3.73(s,3H,-OCH 3 ),4.87(s,1H,CH),4.99(s,1H,OH),6.58(s,2H,ArH),6.60-6.66(m,1H,ArH),6.69-6.77(m,1H,ArH) ,7.06(d,J=8.9Hz,1H,ArH),7.15-7.23(m,3H,ArH),7.34(t,J=7.2Hz,2H,ArH),7.37-7.44(m,3H,ArH) ,7.48(d,J=7.8Hz,2H,ArH),13.27(s,1H,NH). 13 C NMR (CDCl 3, 125MHz) δ194.2, 160.3, 156.5, 152.0, 142.8, 141.6, 137.4, 135.6, 129.1, 128.8, 128.3, 128.0, 126.5, 124.4, 123.4, 122.4, 116.9, 113.3, 112.5, 90.3, 4.7 .HRMS(ESI)m / z calcd for C 37 h 39 NO 4 Na + [M+Na] + 584.2777,found,584.2776.

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Abstract

The invention discloses a preparation method of a 4H-chromene derivative, and belongs to the technical field of organic synthesis. The method comprises the following steps: adding substituted beta-aryl formyl thioamide substituted p-methylene benzoquinone and triethylamine to a reactor, adding solvent ethanol, heating until the reaction is completed, concentrating by a rotary evaporator to obtaina crude product, and isolating the crude product by silica gel column chromatography. The synthesis method of the 4H-chromene derivative has the advantages of being scientific and reasonable, simple in synthesis route, simple in experiment operation, easy in product purifying, and the like. A reaction equation is as shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 4H-chromene derivatives. Background technique [0002] Among various synthetic and naturally occurring heterocyclic structures, the chromene structural unit is one of the most important heterocyclic rings. [0003] 4H-chromene derivatives are widely found in various natural products and medicines, and have significant biological activities. Such as anti-tumor, anti-bacterial and anti-inflammatory, anti-rheumatic and other activities. ((a) Proc. Natl. Acad. Sci. 2000, 97, 7124. (b) Curr. Comput. Aided. Drug. Des. 2016, 12, 34.). [0004] In addition, puerarin and deoxymicroestradiol containing 4H-chromene structure are natural phytoestrogens, which are widely used to improve female aging, treat osteoporosis, relieve female estrogen deficiency, and relieve menopausal symptoms (Nature. 1960, 188, 774.). [0005] In view of the wide a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/58
CPCC07D311/58
Inventor 文丽荣崔涛李明
Owner QINGDAO UNIV OF SCI & TECH