A kind of synthetic method of aryl (chalcogen heteroaryl) methyl sulfone

A synthetic method and a heteroaryl technology are used in the synthesis field of aryl (chalcogenheteroaryl) methyl sulfone, and can solve problems such as no literature reports

Active Publication Date: 2022-08-05
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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  • A kind of synthetic method of aryl (chalcogen heteroaryl) methyl sulfone
  • A kind of synthetic method of aryl (chalcogen heteroaryl) methyl sulfone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] To a 25 mL glass test tube equipped with a stir bar was added benzaldehyde (1.5 mmol), 2-methylthiophene (1 mmol), sulfuric acid (0.5 equiv) and 2 mL of water. The tube was stirred in a preheated oil bath at 60°C for 15 minutes, 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 confirmed that the reaction was 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) to give 2-methyl-5-(phenyl(benzenesulfonyl)methyl) as a white solid after purification Thiophene yield was 82%. The reaction equation is show...

Embodiment 2

[0019] 4-Fluorobenzaldehyde was used to replace the benzaldehyde in Example 1 to obtain a white solid 2-((4-fluorophenyl)(benzenesulfonyl)methyl)-5-methylthiophene in 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 to replace the benzaldehyde in Example 1 to obtain a white solid 2-((2-chlorophenyl)(benzenesulfonyl)methyl)-5-methylthiophene in a yield of 88%.

[0026] 1 H NMR (400MHz, Chloroform-d) δ 8.23–8.16 (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

Sulfones are important pharmaceutical and biologically active compounds. Sulfones are widely used as drugs, such as gamma-secretase inhibitors for the prevention of Alzheimer's disease, and in bioactive compounds, natural products, and agricultural chemicals, such as the now popular herbicide A. Sulfotrione. Sulfones are also most commonly used as intermediates in organic synthesis. On the other hand, chalcogen heterocyclic scaffolds have biological activities such as antineoplastic and antiproliferative drugs. It is well known that thiophene, furan and selenium compounds have various biological activities, such as anti-inflammatory agents, anti-HIV PR inhibitors, NQO2 inhibitors and anticancer agents. This patent develops a simple and efficient Bronsted acid, namely sulfuric acid, which catalyzes the three-component reaction in water to synthesize aryl (chalcogenoheteroaryl) methyl sulfone, with good to high yield and wide substrate range . Our synthetic method is environmentally friendly, economical, and does not require metal catalysis. This sulfone product can be efficiently converted into biocide analogs and arylheteroaryl ketones.

Description

technical field [0001] The patent relates to the research fields of organic synthesis, drug synthesis and organic chemical industry. The specific method is to carry out a three-component reaction of sodium sulfite, aryl / alkyl aldehyde and chalcogen heterocyclic compound to synthesize aryl (chalcogen heteroaryl) in one step. 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. Church, 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, Patent: WO 2010 / 03659...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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