Polysubstituted benzochromone derivative and synthesis method thereof

A technology of benzochromone and synthesis method, which is applied in the field of multi-substituted benzochromone derivatives and their synthesis, can solve the problems of harsh reaction conditions, unstable raw materials, and reduced total yield, and achieve less side reactions and more efficient reactions. Conditions are easy to achieve, the effect of simple operation

Active Publication Date: 2021-06-15
山东博润得新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the synthesis of multi-substituted benzochromone compounds is mainly achieved by derivatization or multi-step condensation reactions of existing chromone skeletons, and it is necessary to pre-functionalize the starting materials or require toxic and unstable raw materials. And the reaction conditions are relatively harsh, not only the process is loaded down with trivial details, but also easily cause side reactions to reduce the total yield

Method used

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  • Polysubstituted benzochromone derivative and synthesis method thereof
  • Polysubstituted benzochromone derivative and synthesis method thereof
  • Polysubstituted benzochromone derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A multi-substituted benzochromone derivative has a structure shown in the following formula Ia, and the reaction scheme is as follows:

[0054]

[0055] The specific preparation steps are as follows: Add dimethylaminovinylacetophenone IIa (35mg, 0.2mmol), diazo compound IIIa (93.7mg, 0.6mmol) into a 25mL reaction tube, [Cp*RhCl 2 ] 2 (5.1mg, 0.008mmol), AgSbF 6 (11mg, 0.032mmol), AgOAc (6.7mg, 0.04mmol), Li 2 CO 3 (30mg, 0.4mmol); N 2 Under protection, dichloromethane (2 mL) was added and reacted at 100° C. for 24 hours. Then separated by silica gel column chromatography (eluent: petroleum ether (boiling point is 60-90°C) / ethyl acetate=10:1, v / v) to obtain yellow liquid Ia (58 mg, yield 78%), the target product Confirmed by NMR and high-resolution mass spectrometry.

[0056] Characterization data of polysubstituted benzochromone derivative Ia:

[0057] Multi-substituted benzochromone derivative Ia, red solid;

[0058] 1 H NMR (400MHz, CDCl 3 )δ8.40(d, J=8.3...

Embodiment 2

[0060] A kind of multi-substituted benzochromone derivatives has a structure shown in the following formula Ib, and the reaction scheme is as follows:

[0061]

[0062] The specific preparation steps are the same as in Example 1, except that the structural formula of the reaction substrate is shown as IIb (41 mg, 0.2 mmol); other steps and conditions are consistent with Example 1.

[0063] In this example, 64 mg of polysubstituted benzochromone derivative Ib was obtained, with a yield of 80%.

[0064] Characterization data of polysubstituted benzochromone derivative Ib:

[0065] Multi-substituted benzochromone derivative Ib, red solid.

[0066] 1 H NMR (400MHz, CDCl 3 )δ8.55(d, J=3.1Hz, 1H), 7.75(d, J=15.0Hz, 1H), 7.08(dd, J=15.0, 3.1Hz, 1H), 4.34(q, J=11.7Hz, 2H), 4.19(q, J=11.8Hz, 2H), 3.81(s, 3H), 2.54(s, 3H), 2.09(s, 3H), 1.28(m, 6H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ184.9, 171.3, 166.5, 163.3, 162.8, 151.3, 143.0, 138.2, 125.3, 123.2, 120.0, 117.7, 115.7, 111.8, 1...

Embodiment 3

[0068] A multi-substituted benzochromone derivative has a structure shown in the following formula Ic, and the reaction scheme is as follows:

[0069]

[0070] The specific preparation steps are the same as in Example 1, except that the structural formula of the reaction substrate is shown as IIc (42 mg, 0.2 mmol); other steps and conditions are consistent with Example 1.

[0071] In this example, 61 mg of polysubstituted benzochromone derivative Ic was obtained, with a yield of 75%.

[0072] Characterization data of polysubstituted benzochromone derivative Ic:

[0073] Multi-substituted benzochromone derivative Ic, red solid.

[0074] 1 H NMR (400MHz, CDCl 3 )δ8.00(d, J=15.0Hz, 1H), 7.78(d, J=3.1Hz, 1H), 7.53(dd, J=15.0, 2.9Hz, 1H), 4.34(q, J=11.7Hz, 2H), 4.19(q, J=11.8Hz, 2H), 2.54(s, 3H), 2.09(s, 3H), 1.28(m, 6H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ184.9, 171.3, 166.5, 163.3, 149.7, 143.2, 140.7, 137.0, 129.1, 128.3, 126.2, 125.1, 123.1, 113.9, 111.8, 61.44, 61.2, 19....

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Abstract

The invention discloses a polysubstituted benzochromone derivative and a synthesis method thereof. Dimethylamino vinyl acetophenone and a diazo compound are used as raw materials, under the conditions of transition metal catalysis, assistant promotion and alkaline additive, the dimethylamino vinyl acetophenone and the diazo compound are subjected to intermolecular cross-coupling cyclization reaction, and the polysubstituted benzochromone derivative is constructed in one step. The method provided by the invention has the advantages of easily available and stable raw materials, wide substrate adaptability, simple preparation method, simple operation, easily realized reaction conditions, safety, environmental protection, one-step construction of chromone ring, few side reactions and high target product yield. Functional groups of the obtained polysubstituted benzochromone derivative have diversity, and the polysubstituted benzochromone derivative is widely applied to the field of medicines.

Description

technical field [0001] The invention relates to a multi-substituted benzochromone derivative and a synthesis method thereof, belonging to the field of drug synthesis. Background technique [0002] Multi-substituted chromones are the basic skeleton of many active natural products and pharmaceutically active molecules; studies have found that there are hundreds of natural products and pharmaceutically active molecules with this skeleton, which have a wide range of biological activities (Mol.Divers.2020, doi:10.1007 / s11030-020-10123-0;Molecules2019,24,1060;Bioorg.Chem.2019,87,560;J.Saudi.Chem.Soc.2017,21,82;Med.Chem.Res.2017,26,691;Med.Chem .Res.2014,23,3187; Eur.J.Med.Chem.2012,54,750), mainly for antibacterial, anti-proliferation and induction of apoptosis, anti-cancer, anti-tumor, anti-convulsant, anti-oxidation, inhibition of aldose reduction Enzyme, molluscicide and treatment of Alzheimer's disease and schizophrenia; in addition, some also exhibit anti-platelet aggregati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/92
CPCC07D311/92
Inventor 娄江柳竹青
Owner 山东博润得新材料有限公司
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