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Synthesis method of aryl(chalcogen-heteroaryl)methyl sulfone

A synthetic method and heteroaryl technology, which is applied in the field of synthesis of aryl (chalcogenoheteroaryl) methyl sulfones, and can solve problems that have not been reported in the literature

Active Publication Date: 2020-06-05
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] As far as we know, there is no similar literature report with this application

Method used

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  • Synthesis method of aryl(chalcogen-heteroaryl)methyl sulfone
  • Synthesis method of aryl(chalcogen-heteroaryl)methyl sulfone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Benzaldehyde (1.5 mmol), 2-methylthiophene (1 mmol), sulfuric acid (0.5 equiv) and 2 mL of water were added to a 25 mL glass test tube equipped with a stir bar. The tube was stirred for 15 minutes in a preheated oil bath at 60°C, then sodium benzenesulfinate (1 mmol) was added slowly. The reaction mixture was stirred at 60 °C. After 7 hours, the progress of the reaction was checked by TLC and the reaction was confirmed to be complete. The reaction mixture was cooled to room temperature. Water (10 mL) was then added to the reaction mixture, which was extracted three times with ethyl acetate (10 mL). The combined organic layers were washed with anhydrous MgSO 4 Dry, filter, and concentrate under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether:ethyl acetate=10:1 as eluent), after purification, 2-methyl-5-(phenyl(benzenesulfonyl)methyl) was obtained as white solid Thiophene yield was 82%. The reaction equation i...

Embodiment 2

[0019] 4-Fluorobenzaldehyde was used instead of benzaldehyde in Example 1 to obtain a white solid 2-((4-fluorophenyl)(benzenesulfonyl)methyl)-5-methylthiophene with a yield of 89%.

[0020] 1 H NMR (400MHz, Chloroform-d) δ7.76–7.33(m,7H),7.12–6.87(m,3H),6.63(dq,J=3.5, 1.1Hz,1H),5.44(s,1H), 2.45(s,3H).

[0021] 13 C NMR (101MHz, cdcl 3 )δ164.23, 161.75, 142.17, 137.30, 133.68, 131.82, 131.74, 130.71, 129.78, 129.09, 128.69, 128.49, 125.15, 115.76, 115.55, 71.64, 15.29.

[0022] HRMS (ESI): calculated for C 18 h 15 FO 2 S 2 Na[M+Na] + =369.0395,foundC 18 h 15 FO 2 S 2 Na[M+ Na] + =369.0373.

[0023] Melting point: 129-130℃.

Embodiment 3

[0025] 2-Chlorobenzaldehyde was used instead of benzaldehyde in Example 1 to obtain a white solid 2-((2-chlorophenyl)(benzenesulfonyl)methyl)-5-methylthiophene with a yield of 88%.

[0026] 1 H NMR (400MHz, Chloroform-d) δ8.23–8.16(m,1H),7.74–7.65(m,2H),7.63–7.55(m,1H),7.47–7.35(m,3H),7.26–7.23 (m,2H),7.00(d,J=3.5Hz,1H),6.66(dd,J=3.6,1.2Hz,1H),6.29(s,1H),2.47(d,J=1.1Hz,3H) .

[0027] 13 C NMR (101MHz, CDCl 3 )δ142.43, 137.63, 134.73, 133.77, 130.99, 130.70, 130.26, 130.13, 130.10, 129.55, 129.08, 128.70, 127.23, 125.15, 66.83, 15.36.

[0028] HRMS (ESI): calculated for C 18 h 15 ClO 2 S 2 Na[M+Na] + =385.0100,foundC 18 h 15 ClO 2 S 2 Na[M +Na] + =385.0089.

[0029] Melting point: 100-101℃.

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Abstract

Sulfone is an important drug and bioactive compound. Sulfone is widely used as a medicament, such as a medicament gamma-secretase inhibitor for preventing Alzheimer's disease, and is widely applied tobioactive compounds, natural products and agricultural chemicals, such as currently popular herbicide mesotrione. Sulfone is also most often used as an intermediate for organic synthesis. On the other hand, a chalcogen heterocyclic stent has biological activity, such as antitumor drugs and antiproliferative drugs. As is well-known, thiophene, furan and selenium compounds have a variety of biological activities, such as anti-inflammatory agents, anti-HIV PR inhibitors, NQO2 inhibitors, and anticancer agents. The invention develops a simple, convenient and efficient Bronsted acid, i.e., sulfuric acid and catalyzed three components react in water to synthesize aryl(chalcogen-heteroaryl)methyl sulfone, the yield is good to be very high, and the substrate range is wide. The synthesis method isenvironment-friendly and economic, and does not need metal catalysis. The sulfone product can be effectively converted into bactericide analogues and aryl heteroaryl ketones.

Description

technical field [0001] This patent relates to the research fields of organic synthesis, drug synthesis and organic chemical industry. The specific method is to carry out three-component reaction of sodium sulfinate, aryl / alkyl aldehyde and chalcogen heterocyclic compound to synthesize aryl (chalcogen heteroaryl base) methyl sulfone compounds. Background technique [0002] Sulfones are widely used as drugs, such as gamma-secretase inhibitors for the prevention of Alzheimer's disease (I. Churcher, D. Beher, J.D. Best, J.L. Castro, E.E. Clarke, A. Gentry, T. Harrison , L. Hitzel, E. Kay, S. Kerrad, H. D. Lewis, P. M. Gutierrez, R. M. Smith, P. J. Oakley, M. Reilly, D. E. Shaw, M. S. Shearman, M. R. Teall, S. Williams and J. D. J. Wrigley, Bioorg. Med. Chem .Lett.,2006,16,280.), also applied to biologically active compounds ((a) G.Andrei, L.Naesens, R.Snoeck and C.E.Stephens, Patent: WO 2012 / 113920; (b) J. M. Caron, Patent: WO 2010 / 141956; (c) P.K. Chakravarty, P.P. Shao, Pate...

Claims

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Application Information

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IPC IPC(8): C07B45/04C07D333/18C07D409/06C07D333/34C07D307/38C07D307/79C07D345/00
CPCC07B45/04C07D333/18C07D409/06C07D333/34C07D307/38C07D307/79C07D345/00
Inventor 曾庆乐库楚酷拉·拉纳卡·雷德郑文婷
Owner CHENGDU UNIVERSITY OF TECHNOLOGY
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