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A kind of preparation method of sulfone compound substituted by β-aryl ketone group

A compound and aryl ketone-based technology, applied in the field of compound synthesis, can solve problems such as limited substituents, harsh reaction conditions, and difficulty in obtaining raw materials, and achieve the effect of easy-to-obtain raw materials, simple operation, and cheap and easy-to-get reaction raw materials

Inactive Publication Date: 2017-10-20
ZHEJIANG UNIV
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Problems solved by technology

However, in the currently reported methods, either the raw materials are difficult to obtain, the reaction conditions are harsh, metal catalysis is required, or the substituents are limited. The above factors have prompted the development of a new class of methods for the construction of β-aryl ketone-substituted sulfone compounds.

Method used

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  • A kind of preparation method of sulfone compound substituted by β-aryl ketone group
  • A kind of preparation method of sulfone compound substituted by β-aryl ketone group
  • A kind of preparation method of sulfone compound substituted by β-aryl ketone group

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: Preparation of 1-phenyl-2-(4-methyl)benzenesulfonyl-1-ketone

[0029] Add 290mg (2mmol) of 1-azidenylbenzene and 744mg (4mmol, 2.0eq.) of p-methylsulfonyl hydrazide to the reaction flask, then add 166mg (1mmol, 0.5eq.) of potassium iodide, 1mL of tert-butyl peroxide Alcohol and 4 mL DMSO were reacted at room temperature for 4 hours. After the TLC plate detects that the raw materials disappear, add water to dilute the system, extract with ethyl acetate, dry the organic phase, evaporate the solvent under reduced pressure, and purify the crude product by column chromatography (eluent: petroleum ether: ethyl acetate = 1:2) A light yellow solid was obtained with a yield of 85%, melting point: 98-99°C,

[0030] Its structural formula is:

[0031]

[0032] 1 H NMR (500MHz, CDCl 3 )δ7.98(d, J=7.5Hz, 2H), 7.79(d, J=8.5Hz, 2H), 7.65(t, J=7.5Hz, 1H), 7.51(t, J=7.5Hz, 2H) ,7.36(d,J=8.0Hz,2H),4.74(s,2H),2.47(s,3H). 13 CNMR (125MHz, CDCl 3 )δ188.3, ​​145.5, 13...

Embodiment 2

[0033] Example 2: Preparation of 1-(3-bromo-4-ethoxy)phenyl-2-(4-methyl)benzenesulfonyl-1-one

[0034] The synthesis method is the same as in Example 1, except that the raw material 1-azidenylbenzene is replaced with 1-azidonyl-(3-bromo-4-ethoxyl)benzene. Light yellow solid, yield 81%, melting point: 97-98°C, its structural formula is:

[0035]

[0036] 1 HNMR (500MHz, CDCl 3 )δ8.09(d,J=2.5Hz,1H),7.93(dd,J=8.5,2.5Hz,1H),7.76-7.72(m,2H),7.34(d,J=8.0Hz,2H), 6.92(d, J=8.5Hz, 1H), 4.63(s, 2H), 4.20(q, J=7.0Hz, 2H), 2.45(s, 3H), 1.52(t, J=7.0Hz, 3H). 13 C NMR (125MHz, CDCl 3 )δ185.6, 160.3, 145.6, 135.8, 134.8, 131.2, 130.0, 129.7, 128.7, 112.8, 112.0, 65.4, 63.7, 21.8, 14.6. HRMS (ESI): m / z calcd for (C 17 h 17 BrO 4 S+H) + :397.0104; found: 397.0108.

Embodiment 3

[0037] Example 3: Preparation of 1-(4-bromo)phenyl-2-(4-methyl)benzenesulfonyl-1-one

[0038] The synthesis method is the same as in Example 1, except that the raw material 1-azidenylbenzene is replaced with 1-azidoenyl-4-bromobenzene. White solid, yield 86%, melting point: 141-142°C, its structural formula is:

[0039]

[0040] 1 H NMR (500MHz, CDCl 3 )δ7.98(d, J=7.5Hz, 2H), 7.79(d, J=8.5Hz, 2H), 7.65(t, J=7.5Hz, 1H), 7.51(t, J=7.5Hz, 2H) ,7.36(d,J=8.0Hz,2H),4.67(s,2H),2.45(s,3H). 13 CNMR (125MHz, CDCl 3 )δ187.4, 145.7, 135.7, 134.6, 132.4, 131.0, 130.1, 130.0, 128.7, 63.9, 21.9. HRMS (ESI): m / z calcd for (C 15 h 13 BrO 3 S+H) + :352.9842; found: 352.9847.

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Abstract

The invention provides a preparation method of beta-arone substituted sulfone compounds. In the method, olefin azide and sulfonyl hydrazide are used as start raw materials; and in an organic solvent, potassium iodide serves as a catalyst while tert-butyl hydroperoxide serves as an oxidizing agent, and the beta-arone substituted sulfone compounds are generated by reactions, wherein the reaction temperature is room temperature, and the reaction time is 2-4 hours. The preparation method provided by the invention has the advantages that the design is reasonable, the raw materials are easily available, no metal catalyst is involved, the reaction conditions are mild, high-temperature backflow is not required, the method is safe and convenient, the yield is high, and the yield of most products is over 70%. The preparation method provided by the invention is an easy-to-operate method for quickly establishing beta-arone substituted sulfone compounds in a mild and diversified manner, wherein the two start raw materials can be obtained by a one-step method, and the reaction raw materials are cheap and easily available. The general formula I of the beta-arone substituted sulfone compounds is shown in the specification.

Description

technical field [0001] The invention belongs to compound synthesis, and mainly relates to a preparation method of sulfone compounds substituted by beta-aryl ketone groups. Background technique [0002] β-aryl keto-substituted sulfones are an important class of chemical intermediates, widely used in Michael addition reactions and Knoevenagel condensation reactions. According to reports in the literature, it can be used to synthesize chalcone [Tetrahedron:Asymmetry 2001,12,513], vinyl sulfone [Tetrahedron:Asymmetry 1998,9,2311], multi-substituted tetrahydropyran [J.Org.Chem.1995,60, 6678] and so on. Therefore, such β-aryl ketone-substituted sulfone compounds are very important intermediates in synthetic chemistry. However, in the currently reported methods, either the raw materials are difficult to obtain, the reaction conditions are harsh, metal catalysis is required, or the substituents are limited. The above factors have prompted the development of a new class of methods ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/24C07C317/44
CPCC07C315/00C07C317/24C07C317/44
Inventor 陈文腾刘星雨陈斌辉邵加安俞永平
Owner ZHEJIANG UNIV
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