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Preparation method for alpha-iodo-beta-arylketo-substituted sulfone compounds

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

Inactive Publication Date: 2016-08-17
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many ways to synthesize it, and it is commonly obtained by substituting α-iodo-β-halogenated ketones with sodium nitrite. However, in the currently reported methods, or the raw materials are difficult to obtain, it is necessary to pre-construct related groups, The harsh reaction conditions, low reaction efficiency, and many by-products have prompted the development of a new class of methods for the construction of α-iodo-β-aryl ketone-substituted sulfone compounds.

Method used

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  • Preparation method for alpha-iodo-beta-arylketo-substituted sulfone compounds
  • Preparation method for alpha-iodo-beta-arylketo-substituted sulfone compounds
  • Preparation method for alpha-iodo-beta-arylketo-substituted sulfone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of 2-iodo-1-phenyl-2-(4-methyl)benzenesulfonyl-1-one

[0029] Add 290 mg (2 mmol) of 1-azidenylbenzene, 744 mg (4 mmol, 2.0 eq.) of p-methylbenzenesulfonyl hydrazide and 664 mg (4 mmol, 2.0 eq.) of potassium iodide into the reaction flask, and then add 1 mL of tert-butyl peroxide Alcohol and 4 mL DMSO-HOAc (V; V=1:1) 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 white solid was obtained with a yield of 85%, melting point: 168-169°C,

[0030] Its structural formula is:

[0031]

[0032] 1 H NMR (500MHz, CDCl 3 )δ7.90(dd, J=12.5,8.0Hz,4H),7.63(t,J=7.5Hz,1H),7.48(t,J=8.0Hz,2H),7.35(d,J=8.0Hz, 2H), 6.52(s, 1H), 2.45(s, 3H). 13 C NMR (125MHz, CDCl 3 )δ18...

Embodiment 2

[0033] Example 2: Preparation of 2-iodo-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. Off-white solid, yield 80%, melting point: 172-173°C, its structural formula is:

[0035]

[0036] 1 H NMR (500MHz, CDCl 3 )δ8.08(d, J=2.0Hz, 1H), 7.90(dd, J=8.5, 2.5Hz, 1H), 7.86(d, J=8.0Hz, 2H), 7.35(d, J=8.0Hz, 2H), 6.90(d, J=8.5Hz, 1H), 6.42(s, 1H), 4.19(q, J=7.0Hz, 2H), 2.45(s, 3H), 1.51(t, J=7.0Hz, 3H). 13 C NMR (125MHz, CDCl 3 )δ185.7, 160.4, 146.3, 134.8, 132.2, 131.0, 130.9, 129.7, 128.7, 127.1, 112.9, 112.1, 65.5, 38.2, 21.9, 14.6. HRMS (ESI): m / zcalcd for (C 17 h 16 BrIO 4 S+H) + :522.9070; found: 522.9074.

Embodiment 3

[0037] Example 3: Preparation of 2-iodo-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. Off-white solid, yield 86%, melting point: 147-148°C, its structural formula is:

[0039]

[0040] 1 H NMR (500MHz, DMSO) δ7.89-7.88(m, 2H), 7.83(d, J=8.0Hz, 2H), 7.73-7.71(m, 2H), 7.45(s, 1H), 7.41(d, J=8.0Hz,2H),2.38(s,2H). 13 C NMR (125MHz, DMSO) δ189.0, 145.2, 133.1, 132.5, 132.0, 130.8, 129.6, 129.5, 128.8, 39.2, 21.2. HRMS (ESI): m / z calcd for (C 15 h 12 BrIO 3 S+H) + :478.8808; found: 478.8809.

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Abstract

The invention provides a preparation method for alpha-iodo-beta-arylketo-substituted sulfone compounds. The preparation method comprises the following steps: taking olefin nitrine, sulfohydrazide and potassium iodide as starting raw materials; and in an organic solvent, taking tert-butyl hydroperoxide as an oxidizing agent, and reacting to generate the alpha-iodo-beta-arylketo-substituted sulfone compounds, wherein a molar ratio of olefin nitrine to sulfohydrazide to potassium iodide to tert-butyl hydroperoxide is 1:2:2:2, the reaction temperature is the room temperature, and the reaction time is 2-4 hours. The preparation method provided by the invention is reasonable in design, adopts easily available raw materials, does not need a metal catalyst, is gentle in reaction condition, is free of high-temperature flux, is safe and convenient and is high in yield, and the yield of most products is 70% or higher, so that the preparation method is a method, which is simple to operate, quick, gentle and diversified, for constructing the alpha-iodo-beta-arylketo-substituted sulfone compounds, wherein the three starting raw materials can be obtained through a one-step process, and the reaction raw materials are cheap and easily available; and the formulas of the alpha-iodo-beta-arylketo-substituted sulfone compounds are as shown in the specification.

Description

technical field [0001] The invention belongs to compound synthesis, and mainly relates to a preparation method of α-iodo-β-aryl ketone-substituted sulfone compounds. Background technique [0002] α-iodo-β-aryl ketone substituted sulfone compounds are reported to exist in many natural product skeletons, and have good pharmacodynamic properties and important physiological activities. Such derivatives are a very important class of compounds in medicinal chemistry. There are many ways to synthesize it, and it is commonly obtained by substituting α-iodo-β-halogenated ketones with sodium nitrite. However, in the currently reported methods, or the raw materials are difficult to obtain, it is necessary to pre-construct related groups, The harsh reaction conditions, low reaction efficiency, and many by-products have prompted the development of a new method for the construction of α-iodo-β-aryl ketone-substituted sulfone compounds. Contents of the invention [0003] The object of ...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/24C07C317/44
CPCC07C315/00C07C317/24C07C317/44
Inventor 陈文腾陈恩舒可邵加安俞永平
Owner ZHEJIANG UNIV
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