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Method for preparing benzo-6, 8-dihydroisoquinoline-1-selenious sulfuryl benzamide compound through bimetallic catalysis

A technology of sulfone benzamide and dihydroisoquinoline, which is applied in the field of chemical intermediate preparation and can solve problems such as non-conformity, destruction, and low reaction efficiency

Inactive Publication Date: 2021-07-13
JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The reported preparation method of benzo-6,8-dihydroisoquinoline-1-selenosulfonyl benzamide is mainly obtained through multi-step coupling and oxidation, which has many reaction steps and low reaction efficiency And the reaction process is easy to generate a series of intractable by-products and other shortcomings, causing irreversible pollution and damage to the environment, which does not meet the requirements of modern green synthesis

Method used

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  • Method for preparing benzo-6, 8-dihydroisoquinoline-1-selenious sulfuryl benzamide compound through bimetallic catalysis
  • Method for preparing benzo-6, 8-dihydroisoquinoline-1-selenious sulfuryl benzamide compound through bimetallic catalysis
  • Method for preparing benzo-6, 8-dihydroisoquinoline-1-selenious sulfuryl benzamide compound through bimetallic catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of product 4a

[0037] At room temperature, add 10mmol of 1,2,3,4-tetrahydroisoquinoline, 15mmol of sodium selenide and 10mmol of 2-bromobenzaldehyde in a 50mL round bottom flask, then add 30mL of DMSO and 1mmol of acetic acid Magnesium, 1 mmol of copper acetate, and 20 mmol of cesium carbonate were stirred at 100° C. for 24 hours. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain The pure product of benzo-6,8-dihydroisoquinoline-1-selensulfonylbenzamide compound 4a.

[0038] 4a 1 H NMR spectrum see figure 1 , 13 C NMR spectrum see figure 2 .

[0039] 5,13a-Dihydro-6H,8H-benzo[5,6][1,3]selenazino[2,3-a]isoquinolin-8-one 13-oxide(4a)White solid(81%);mp:83 -85°C;

[0040] 1 H NMR (CDCl 3 ,500MHz)δ8.19-8.17(d,J=8.0Hz,1H),7.42-7.38(m,2H),7.34-7.29(m,4...

Embodiment 2

[0043] Embodiment 2: the preparation of product 4b

[0044]At room temperature, add 10mmol of 1,5-methyl-2,3,4-tetrahydroisoquinoline, 15mmol of sodium selenide and 10mmol of 2-bromobenzaldehyde in a 50mL round bottom flask, and then add 30mL of DMSO, 1 mmol of magnesium acetate and 1 mmol of copper acetate, and 20 mmol of cesium carbonate were stirred at 100°C for 24 hours. After cooling, add 20 mL of saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain The pure product of benzo-6,8-dihydroisoquinoline-1-selensulfonylbenzamide compound 4b.

[0045] 4b 1 H NMR spectrum see image 3 , 13 C NMR spectrum see Figure 4 .

[0046] 3-Methoxy-5,13a-dihydro-6H,8H-benzo[5,6][1,3]selenazino[2,3-a]isoquinolin-8-one 13-oxide(4b)Yellow oil(73%) ;

[0047] 1 H NMR (CDCl 3 ,500MHz)δ8.16(d,J=7.5Hz,1H),7.38(dd,J=7.5Hz,1.5Hz,1H),7.3...

Embodiment 3

[0049] Embodiment 3: the preparation of product 4c

[0050] At room temperature, in a 50mL round bottom flask, add 10mmol 1,2,3,4-tetrahydroisoquinoline, 15mmol sodium selenide and 10mmol 2-bromo-2-methylbenzaldehyde, and then add 30mL DMSO, 1 mmol of magnesium acetate and 1 mmol of copper acetate, and 20 mmol of cesium carbonate were stirred at 100°C for 24 hours. After cooling, add 20mL saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 20mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain by 200-300 mesh silica gel column chromatography The pure product of benzo-6,8-dihydroisoquinoline-1-selensulfonylbenzamide compound 4c.

[0051] 4c 1 H NMR spectrum see Figure 5 , 13 C NMR spectrum see Image 6 .

[0052] 12-Methyl-5,13a-dihydro-6H,8H-benzo[5,6][1,3]selenazino[2,3-a]isoquinolin-8-one 13-oxide(4c)Pale yellow solid(89% );mp:75-77℃;

[0053] 1 H NMR (CDCl 3 ,500MH...

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Abstract

The invention discloses a method for preparing a benzo-6, 8-dihydroisoquinoline-1-selenious sulfuryl benzamide compound as shown in a formula (IV) through bimetallic catalysis. The preparation method comprises the following steps: fully reacting 1,2,3,4 tetrahydroisoquinoline compound shown in a formula (I), sodium selenide compound shown in a formula (II) and 2 -bromobenzaldehyde compound shown in a formula (III) in DMSO solvent with magnesium acetate and copper acetate as catalysts and cesium carbonate as alkali, and treating the product to obtain benzo -6,8- dihydroisoquinoline- 1- selenious sulfonylbenzamide compound. The method has the advantages of low cost, simplicity in operation, excellent yield, meeting of green synthesis requirements and the like, and is suitable for industrial synthesis of drug intermediates related to dihydroisoquinoline compounds.

Description

technical field [0001] The invention belongs to the technical field of preparation of chemical intermediates, and in particular relates to a method for preparing benzo-6,8-dihydroisoquinoline-1-selenosulfonyl benzamides by bimetallic catalysis. Background technique [0002] Dihydroisoquinoline derivatives are an important class of pharmaceutical and chemical intermediates. For example, they have various biological activities, including anti-tumor, antibacterial, analgesic, immune function regulation, anti-platelet aggregation, anti-arrhythmia, antihypertensive, etc. , have been used to synthesize a series of important drugs. Most of the isoquinoline alkaloid drugs have basic structures such as dihydroisoquinoline or isoquinoline derivatives. Therefore, such drugs can basically be further synthesized from simple dihydroisoquinoline derivatives come out. Benzo-6,8-dihydroisoquinoline-1-selensulfonyl benzamide compounds have good storage stability, and are suitable for the pr...

Claims

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Application Information

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IPC IPC(8): C07D517/04
CPCC07D517/04
Inventor 徐润生程依赢吴亦凤蔡荣荣
Owner JIYANG COLLEGE OF ZHEJIANG A & F UNIV
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