Preparation method of 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compound

A technology of dihydrocyclopentane and diphenylcyclopropenone, which is applied in the field of chemistry and can solve problems such as complex structure of chromone skeleton and the like

Active Publication Date: 2021-06-04
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the deficiencies in the prior art, the present invention provides a method for taking cyclopropenone as the only carbonyl source to participate in the carbonylation reaction, and provides 1,2-dihydro Preparation method of cyclopentano[b]chromene-3,9-dione compound, which solves the problem of preparation method of polycyclic compound with complex structure chromone skeleton

Method used

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  • Preparation method of 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compound
  • Preparation method of 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compound
  • Preparation method of 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compound

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Embodiment 1

[0019] The embodiment of the present invention provides a preparation method of 1,2-dihydrocyclopenta[b]chromene-3,9-dione compound, using 1,2-dihydrocyclopenta[b]chromene-3 , 9-diketone compound 4a is an example, the raw materials used and the preparation method are:

[0020]

[0021] 3-iodochromone (0.2mmol), diphenylcyclopropenone (42.1mg, 0.2mmol), norbornene (0.8mmol, 75.3mg), cesium carbonate (130.4mg, 0.4mmol), palladium chloride (3.5mg, 0.02mmol), P(4-CF 3 -C 6 h 4 )3 (18.7mg, 0.04mmol), 2.0mL of fluorobenzene was added to a 4mL reaction flask, and reacted at 100°C for 24 hours. =40:1~5:1) (separation method is column chromatography separation) to obtain yellow solid 4a, its yield is 48.5mg, yield rate is 91%, melting point is 116.7~118.5 ℃, spectral data is: 1 H NMR (400MHz, CDCl 3 )δ8.07(dd, J=8.0,1.6Hz,1H),7.62(ddd,J=8.8,7.2,1.6Hz,1H),7.44(d,J=8.2Hz,1H),7.35–7.30(m ,1H),2.99(d,J=5.4Hz,1H),2.53(d,J=4.0Hz,1H),2.43(d,J=4.0Hz,1H),2.36(d,J=5.2Hz,1H ),1.64(tt,J=...

Embodiment 2

[0023] Taking the preparation of 1,2-dihydrocyclopenta[b]chromene-3,9-dione compound 4b with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0024]

[0025] In Example 1, the 3-iodochromone used was replaced with equimolar 3-iodo-5-methoxychromone, and the other steps were the same as in Example 1 to obtain a yellow solid 4b, the yield of which was 30.3 mg, and the yield It is 51%, the melting point is 163.8~165.0℃, and the spectral data is: 1 H NMR (400MHz, CDCl 3 )δ7.60(t, J=8.4Hz, 1H), 7.13(d, J=8.4Hz, 1H), 6.84(d, J=8.4Hz, 1H), 3.98(s, 3H), 3.06(d, J=5.2Hz, 1H), 2.67(d, J=3.8Hz, 1H), 2.53(d, J=3.4Hz, 1H), 2.43(d, J=5.2Hz, 1H), 1.80–1.69(m, 1H),1.67–1.58(m,1H),1.52–1.43(m,1H),1.39–1.30(m,1H),1.05(d,J=11.0Hz,1H),0.98(d,J=11.0Hz ,1H); 13 C NMR (100MHz, CDCl 3 )δ202.6, 177.7, 160.4, 158.3, 157.9, 142.9, 135.2, 115.9, 111.0, 107.0, 56.6, 53.4, 42.3, 39.8, 37.3, 32.1, 29.0, 28.7; HRMS (ESI-TOF): calcd.fo...

Embodiment 3

[0027] Taking the preparation of 1,2-dihydrocyclopenta[b]chromene-3,9-dione compound 4c with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0028]

[0029] In Example 1, the 3-iodochromone used was replaced with equimolar 3-iodo-5-fluorochromone, and the other steps were the same as in Example 1 to obtain a yellow solid 4c with a yield of 35.3 mg and a yield of 62%, the melting point is 168.7~170.1℃, and the spectral data is: 1 H NMR (400MHz, CDCl 3)δ7.66(td, J=8.4,5.6Hz,1H),7.39(d,J=8.6Hz,1H),7.09(dd,J=10.2,8.6Hz,1H),3.09(d,J=5.2 Hz, 1H), 2.66(d, J=4.0Hz, 1H), 2.56(d, J=3.6Hz, 1H), 2.46(d, J=5.2Hz, 1H), 1.76(tt, J=11.8, 4.2 Hz,1H),1.65(tt,J=12.0,4.2Hz,1H),1.53–1.44(m,1H),1.41–1.32(m,1H),1.08(d,J=11.0Hz,1H),0.98 (d,J=11.0Hz,1H); 13 C NMR (100MHz, CDCl 3 )δ202.2, 176.3, 161.1(d, J=266.2Hz), 158.7, 157.2, 142.2, 135.1(d, J=10.9Hz), 115.7(d, J=10.5Hz), 115.1(d, J=4.6Hz) ,112.8(d,J=20.7Hz),53.36,42.22,39...

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Abstract

The invention provides a preparation method of a 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compound, and relates to the technical field of chemistry. According to the preparation method of the 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compound, 3-iodo chromone, norbornene and cyclopropenone are taken as raw materials, and a [2 + 2 + 1] series cyclization reaction is carried out in an organic solvent under the condition of a palladium catalyst, so a series of 1, 2-dihydrocyclopenta [b] chromene-3, 9-diketone compounds are synthesized; the compounds contain a chromone skeleton with potential biological activity, can provide a compound source for biological activity screening, and have important application value in the field of medicinal chemistry. Meanwhile, cyclopropenone is used as a unique carbonyl source to participate in the palladium-catalyzed carbonylation reaction for the first time, and a new method is provided for the palladium-catalyzed carbonylation reaction for synthesizing carbonyl compounds.

Description

technical field [0001] The invention relates to the technical field of chemistry, in particular to a method for preparing 1,2-dihydrocyclopenta[b]chromene-3,9-dione compounds. Background technique [0002] The introduction of the heterocyclic structure into the drug molecule can reduce its lipophilicity and improve its solubility, thereby enhancing the efficacy of the drug. As a kind of oxygen-containing unit, chromone skeleton widely exists in drug molecules. Therefore, the development of low-cost, simple and efficient methods to realize the synthesis of chromone skeleton compounds is of great significance for the development of new drugs and the enrichment of organic synthesis methodologies. [0003] For decades, many scientists in the field of synthesis have explored the synthesis methods of new compounds and achieved fruitful results. Among them, the use of transition metal palladium to catalyze the synthesis of new compounds is booming. [0004] However, we have noti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/00
CPCC07D311/00C07B2200/13
Inventor 韩文勇朱文庆方雨辰李菲杨敏鸽陈永正
Owner ZUNYI MEDICAL UNIVERSITY
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