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3-(1-hydroxyalkylene) indolone and preparation method thereof
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A technology of hydroxyalkylene and indolinone, which is applied in antibacterial drugs, antipyretics, organic chemistry, etc., can solve the problems of strict reaction conditions, unfavorable large-scale production and use, and expensive photocatalysts, etc., and achieves a synthetic route Short, easy-to-use effects
Pending Publication Date: 2022-02-01
YANBIAN UNIV
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[0004] The present invention will solve the photocatalyst that exists in the method for synthesizing 3-(1-hydroxyalkylene) indolinone by dicarbonyl sulfideylide as carbene precursor under the photocatalyst action of precious metal Ir in the prior art, and the price is expensive, and the reaction Strict conditions, unfavorable for large-scale production and use of technical problems, provide a kind of 3-(1-hydroxyalkylene)indolinone and its preparation method
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[0031] Put N-(4-chlorophenyl)-2-(dimethyl(oxo)-16-thioylide)-N-methyl-3-oxopropionamide (60mg) into a 10mL reaction tube and Add 2 mL of dry 1,2-dichloroethane, add dichloro(pentamethylcyclopentadienyl) rhodium (5 mg), and stir the reaction at 100° C. for 20 h. After filtration, the filtrate was spun to remove the solvent and separated by a silica gel column to obtain a light yellow solid. 31 mg, 69% yield, R f =0.42(PE / EA=2:1,v / v). 1 H NMR (300MHz, Chloroform-d) δ12.09 (br.s, 1H), 7.34–7.24 (m, 1H), 7.17 (dd, J=8.3, 2.0Hz, 1H), 6.84 (d, J=8.4 Hz,1H),3.32(s,3H),2.44(s,3H). 13 C NMR (75MHz,Chloroform-d)δ174.3,170.8,137.2,127.6,124.8,123.6,119.7,109.1,101.2,25.8,20.4,
[0034] According to the method described in Example 1, using N-phenyl-2-(dimethyl(oxo)-16-thioylide)-N-benzyl-3-oxopropionamide (66 mg) as starting material, to obtain 1-Phenyl-3-(1-hydroxyvinyl)-1-methylindol-2-one, yellow solid, 35mg, yield 69%, R f =0.58(PE / EA=2:1,v / v). 1 H NMR (300 MHz, Chloroform-d) δ13.59(br.s,1H),7.42–7.36(m,1H),7.33–7.26(m,5H), 7.15–7.05(m,2H),6.86( dd,J=7.0,1.9Hz,1H),5.06(s,2H),2.49(s,3H); 13 C NMR (75MHz, Chloroform-d) δ173.3, 171.1, 138.1, 136.1, 128.8, 127.6, 127.2, 125.2, 122.4, 122.2, 119.8, 109.4, 101.7, 43.3, 20.4.
Embodiment 3
[0036] 3-(1-Hydroxyvinyl)-1,5-dimethylindol-2-one
[0037] According to the method described in Example 1, with N-(4-methylphenyl)-2-(dimethyl (oxo)-16-thioylide)-N-methyl-3-oxopropionamide ( 56mg) as raw material to obtain 3-(1-hydroxyvinyl)-1,5-dimethylindol-2-one, yellow solid, 30mg, yield 74%, R f =0.37(PE / EA=2:1,v / v). 1H NMR (300MHz, Chloroform-d)δδ13.44(br.s,1H),7.17(s,1H),7.03(d,J=8.0Hz,1H),6.83(d,J=8.0Hz,1H) ,3.32(s,3H),2.44(s,3H),2.40(s,3H).;. 13 C NMR (75MHz, Chloroform-d) δ172.5, 171.0, 136.7, 131.4, 125.6, 122.2, 120.4, 108.0, 101.6, 50.7, 21.4, 20.2.
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Abstract
The invention relates to 3-(1-hydroxyalkylene) indolone and a preparation method thereof, and belongs to the technical field of organic synthesis. The technical problem that an existing synthetic method of 3-(1-hydroxyalkylene) indolone is not beneficial to large-scale production and use is solved. The 3-(1-hydroxyalkylene) indolone is obtained by carrying out intramolecular carbeneinsertion reaction on dicarbonyl oxysulfide ylide as shown in a formula [2], and the structural formula is as shown in a formula [1]; wherein R1, R2 and R3 independently represent an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, a cycloalkyl alkyl group having 4 to 15 carbon atoms, an aryl group having 6 to 15 carbon atoms or an aralkyl group having 7 to 15 carbon atoms. The dicarbonyl oxysulfide ylide compound is adopted as the raw material, the raw material is simple and easy to obtain, tedious operation is not needed, and the method is a simple method suitable for large-scale preparation. The 3-(1-hydroxyalkylene) indolone provided by the invention is a kind of very important organic intermediates and drug intermediates.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a 3-(1-hydroxyalkylene)indolinone and a preparation method thereof. Background technique [0002] 3-(1-Hydroxyalkylene)indolinones are a very important class of organic intermediates, which are widely used in the fields of medicinal chemistry and synthetic chemistry. In medicinal chemistry, 3-(1-hydroxyalkylene) indolones exhibit many biological activities, such as the antirheumatic drug Tenidap (Márta Porcs-Makkay, Gyula Simig.Organic Process Research & Development, 2000) developed by Pfizer ,4,10.), is a class of non-steroidal anti-inflammatory analgesic drugs containing 3-(1-hydroxyalkylene)indolinone structure, which can inhibit cyclooxygenase and lipoxygenase, regulate cytokine activity , can also effectively reduce the acute phase response indicators such as serum amyloid, C-reactive protein, erythrocyte sedimentation rate and interleukin-6, and the t...
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