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A kind of synthetic method of polychloromethyl substituted dihydroisoquinolinone compound

A technology of isoquinolinone and polychloromethyl, which is applied in the field of synthesis of polychloromethyl-substituted dihydroisoquinolinone compounds, can solve the problems of low functional group diversity and cumbersome operation, and achieve a single reaction system, Effects from a wide range of sources and easy processing

Active Publication Date: 2021-09-24
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional method of synthesizing dihydroisoquinolinone is to obtain it through the condensation reaction of phthalic anhydride and imine under acid or base catalysis or under heating conditions. The operation is cumbersome and the diversity of functional groups is not high.

Method used

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  • A kind of synthetic method of polychloromethyl substituted dihydroisoquinolinone compound
  • A kind of synthetic method of polychloromethyl substituted dihydroisoquinolinone compound
  • A kind of synthetic method of polychloromethyl substituted dihydroisoquinolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add N-methyl-N-(2-methallyl)benzamide 1a (0.2 mmol), dichloromethane 2a (2 mL), di-tert-butyl peroxide (3 equivalents) to a Schlenk reaction tube In, sealed. Heating to 120°C, the reaction time was 20 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3aa was obtained by column chromatography with a yield of 75%. 1 H NMR (CDCl 3 , 400 MHz):δ 8.14 (d, J = 7.7 Hz, 1H), 7.53-7.49 (m, 1H), 7.42-7.38 (m, 1H), 7.31 (d, J = 7.7 Hz, 1H), 5.51-5.48 (m, 1H), 3.52 (d, J = 12.8 Hz, 1H), 3.37 (d, J =12.8 Hz, 1H), 3.17 (s, 3H), 2.68-2.59 (m, 2H), 1.52 (s, 3H). 13 C NMR (CDCl 3 ,100 MHz): δ 164.5, 143.0, 132.3, 129.1, 128.3, 127.9, 124.3, 70.2, 58.4,51.8, 37.7, 35.4, 22.8.

Embodiment 2

[0024] Add N,4-dimethyl-N-(2-methallyl)benzamide 1b (0.2 mmol), dichloromethane 2a (2 mL), di-tert-butyl peroxide (4 equivalents) to Schlenk reaction tubes, sealed. Heating to 120°C, the reaction time was 12 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3ba was obtained by column chromatography with a yield of 73%. 1 H NMR (CDCl 3 , 400MHz): δ 8.02 (d, J = 7.9 Hz, 1H), 7.19 (d, J = 7.9 Hz, 1H), 7.09 (s, 1H),5.51-5.48 (m, 1H), 3.49 (d, J = 12.8 Hz, 1H), 3.35 (d, J = 12.8 Hz, 1H), 3.16(s, 3H), 2.63-2.61 (m, 2H), 2.42 (s, 3H), 1.50 (s, 3H). 13 C NMR (CDCl 3 , 100MHz): δ 164.7, 143.1, 142.9, 129.2, 128.6, 125.7, 124.9, 70.3, 58.4, 51.8,37.6, 35.3, 22.8, 22.0.

Embodiment 3

[0026] N-methyl-4-ethyl-N-(2-methallyl)benzamide 1c (0.2 mmol), dichloromethane 2a (1 mL), tert-butyl peroxybenzoate (3 equiv.) Add to a Schlenk reaction tube and seal. It was heated to 110°C and the reaction time was 20 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3ca was obtained by column chromatography with a yield of 69%. 1 H NMR (CDCl 3 , 400 MHz): δ 8.06 (d, J = 7.9 Hz, 1H), 7.23 (d, J = 7.9 Hz, 1H), 7.12(s, 1H), 5.49-5.46 (m, 1H), 3.51 (d, J = 12.8 Hz, 1H), 3.35 (d, J = 12.8 Hz,1H), 3.17 (s, 3H), 2.73-2.68 (m, 2H), 2.66-2.59 (m, 2H), 1.52 (s, 3H), 1.27(t, J = 7.6 Hz, 1H). 13 C NMR (CDCl 3 , 100 MHz): δ 164.7, 149.1, 143.1, 129.3,127.4, 125.9, 123.7, 70.4, 58.5, 51.8, 37.7, 35.3, 29.3, 22.8, 15.5.

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Abstract

The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of a polychloromethyl-substituted dihydroisoquinolinone compound. In the presence of an oxidizing agent, the method uses N-allyl aromatic formamide compound as a raw material, and two Chloromethane or chloroform undergoes free radical reaction to obtain polychloromethyl-substituted dihydroisoquinolinone compounds. The operation method is simple, easy to separate and purify, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of a polychloromethyl-substituted dihydroisoquinolinone compound. Background technique [0002] Isoquinolinone compounds widely exist in nature. Studies in recent years have found that isoquinolinone derivatives have various biological activities such as relaxing blood vessels, anti-tumor, bactericidal, and anti-diabetic. Based on this, the research on the synthesis method of this kind of structure is an important aspect of organic chemistry research. The traditional method for synthesizing dihydroisoquinolinone is to obtain it through the condensation reaction of phthalic anhydride and imine under acid or base catalysis or under heating conditions, which is cumbersome to operate and has low functional group diversity. In recent years, due to the rapid development of transition metal-catalyzed organic reactions, metal-catalyzed methods f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/24C07D495/04
CPCC07D217/24C07D495/04
Inventor 潘长多袁成吴超
Owner JIANGSU UNIV OF TECH