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A kind of method of synthesizing e alkenyl sulfone compound

A technology of compound and alkenyl sulfone, which is applied in the field of synthesizing E-alkenyl sulfone compound by catalytic degradation of benzenesulfonyl hydrazone with iodobenzene diacetate, can solve the problems such as not having environmental friendliness, and achieve low reaction toxicity and high reaction efficiency. The effect of mild conditions and high product yield

Active Publication Date: 2017-05-17
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, Wang Yongqiang et al. reported that copper acetate was used as a catalyst to make benzenesulfonylhydrazone undergo a free radical reaction process to generate E-alkenyl sulfone compounds. The reaction substrate is wider and the product yield is higher, but transition metals are still used to participate in the reaction. Not environmentally friendly (Shuai Mao, Ya-Ru Gao, Xue-QingZhu, Dong-Dong Guo and Yong-Qiang Wang*, Copper-catalyzed radical reaction of N-tosylhydrazones: Stereoselective synthesis of(E)-vinyl sulfones.Org. Lett., 2015, 17, 1692-1695.)

Method used

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  • A kind of method of synthesizing e alkenyl sulfone compound
  • A kind of method of synthesizing e alkenyl sulfone compound
  • A kind of method of synthesizing e alkenyl sulfone compound

Examples

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Comparison scheme
Effect test

Embodiment 1

[0023] Implementation Example 1: Add 64mg (0.2mmol) benzenesulfonylhydrazone compound 1a, 71mg (0.22mmol) PhI(OAc) in a round bottom flask 2 and 28 mg (0.2 mmol) K 2 CO 3 , adding 2mL of DMF, in an oil bath at 80°C, reacting with magnetic stirring for 4h, and monitoring the progress of the reaction by TLC. After the reaction, extract with ethyl acetate and separate by column chromatography [petroleum ether (60~90°C) / ethyl acetate=15 / 1] to obtain (E)-1-methyl-4-(4-methylbenzene Vinyl)sulfonylbenzene 2a, white solid 45mg, yield 83%, Mp: 92-94℃. 1 H NMR (400MHz, CDCl 3 )δ7.87(d,J=6.4Hz,2H,ArH)7.68(d,J=12.0Hz,1H,CH),7.42(m,4H,ArH),7.24–7.22(m,2H,ArH), 6.84(d,J=12.0Hz,1H,CH),2.47(s,3H,CH 3 ),2.41(s,3H,CH 3 ); 13 C NMR (100MHz, CDCl 3 )δ148.11, 145.09, 131.55, 130.42, 129.17, 129.14, 128.09, 115.86, 115.68, 22.04, 21.70. MS (ESI): m / z = 294.9 [M + Na] + ,567.0[2M+Na] + The reaction principle of implementation example 1 is as follows:

[0024]

Embodiment 2

[0025] Implementation Example 2: Add 64mg (0.2mmol) benzenesulfonylhydrazone compound 1a, 71mg (0.22mmol) PhI(OAc) in a round bottom flask 2 and 28 mg (0.2 mmol) K 2 CO 3 , adding 2mL of DMF, under the condition of 100°C in an oil bath, magnetically stirred for 4h, and monitored the progress of the reaction by TLC. After the reaction, extract with ethyl acetate and separate by column chromatography [petroleum ether (60~90°C) / ethyl acetate=15 / 1] to obtain (E)-1-methyl-4-(4-methylbenzene Vinyl)sulfonylbenzene 2a, white solid 38mg, yield is 70%, the reaction principle of implementation example 2 is as follows:

[0026]

Embodiment 3

[0027] Implementation Example 3: Add 64mg (0.2mmol) benzenesulfonylhydrazone compound 1a, 71mg (0.22mmol) PhI(OAc) in a round bottom flask 2 and 28 mg (0.2 mmol) K 2 CO 3 , adding 2mL of DMF, in an oil bath at 80°C, reacting with magnetic stirring for 2h, and monitoring the progress of the reaction by TLC. After the reaction, extract with ethyl acetate and separate by column chromatography [petroleum ether (60~90°C) / ethyl acetate=15 / 1] to obtain (E)-1-methyl-4-(4-methylbenzene Vinyl)sulfonylbenzene 2a, white solid 41mg, yield is 75%, the reaction principle of implementation example 3 is as follows:

[0028]

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Abstract

The invention discloses a method for synthesizing an E-alkenyl sulfone compound, which comprises the following steps: dissolving phenylsulfonyl hydrazone in a DMF (N,N-dimethylformamide) solvent, adding iodobenzene diacetate and potassium carbonate, and reacting at 80 DEG C for 4 hours; and after the reaction finishes, extracting, and carrying out column chromatography separation to obtain the E-alkenyl sulfone compound. The iodobenzene diacetate is used for catalyzing the degradation reaction of the phenylsulfonyl hydrazone in the method. The reaction uses the non-metal catalyst, and thus, has the advantages of environment friendliness, mild reaction conditions, short time, simple after-treatment process and high product yield. The E-alkenyl sulfone compound can be used as a useful synthon, and has potential pharmaceutical activity and wide applicability.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry and relates to a method for synthesizing E-alkenyl sulfone compounds, in particular to a method for synthesizing E-alkenyl sulfone compounds by catalytically degrading benzenesulfonyl hydrazone with iodobenzene diacetate. Background technique [0002] Alkenyl sulfone compounds are widely used. It is an important class of synthons in synthetic chemistry, participating in a variety of reactions, such as acting as a Michael acceptor and playing the role and function of a dienophile in the D-A cycloaddition reaction; at the same time, alkenyl sulfone compounds have potential Biological activity, such as substituted vinyl sulfone compounds have been found to have good biological activity on various cysteineases, which can be used as their potential and powerful inhibitors, and can also be used as HIV-1 integrase inhibitors, etc.; It has recently been found that alkenyl sulfone compounds also...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/14C07C315/00C07D307/38
Inventor 罗再刚赵禹方玉玉徐雪梅沈洪芳
Owner ANHUI UNIV OF SCI & TECH
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