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Synthesis method of pyrrolo [3, 4-c] quinoline-1, 3-diketone compound

A synthesis method, 4-c technology, applied in the direction of organic chemistry, etc., can solve problems such as difficulty in expanding new compounds with novel structures, limiting product derivatization, negative environmental impact, etc., achieving low production cost, fast reaction rate, Mild effect of synthetic conditions

Active Publication Date: 2021-02-12
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Indoledione is generally used as a substrate in the above methods for synthesizing pyrrolo[3,4,c]quinoline-1,3-dione, which limits the derivatization of the product, and it is difficult to expand the novel structure and bioavailable Activity Screening of New Compounds
Some methods use expensive metal catalysts, or difficult-to-obtain reaction substrates, which increase costs on the one hand and have a great negative impact on the environment on the other hand
These shortcomings hinder the application of the above synthetic methods to industrial production.

Method used

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  • Synthesis method of pyrrolo [3, 4-c] quinoline-1, 3-diketone compound
  • Synthesis method of pyrrolo [3, 4-c] quinoline-1, 3-diketone compound
  • Synthesis method of pyrrolo [3, 4-c] quinoline-1, 3-diketone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0025]Example 1: 8-Methyl-1,3-dioxo-2-phenyl-2,3-dihydro-1H-pyrrolo[3,4-c]quinoline-4-carboxylic acid methyl ester

[0026]

[0027]Add the magneton to the 10 ml reaction tube, and then add the raw materials (4-methyl-phenylamino)-methyl acetate (0.1 mmol) and N-phenylmaleimide (0.3 mmol), Ru(bpy )3Cl2 (0.001 mmol), TBHP (0.4 mmol), 0.5ml solvent (DMSO), after reacting under blue light irradiation at room temperature for 12 hours, extraction, concentration, drying, and column chromatography separation (silica gel: 200~300 mesh, eluent The volume ratio is petroleum ether: ethyl acetate=20:1), and the pure white solid product is obtained, which is 2-(tert-butyl)-8-methyl-1,3-diox-2-,3-dihydro Synthesis of -1H-pyrrolo[3,4-c]quinoline-4-carboxylic acid methyl ester with a yield of 71%.

[0028]The NMR data of the compound are as follows:1H NMR (600 MHz, cdcl3) δ 8.73 (s, 1H), 8.23 ​​(d,J = 8.8 Hz, 1H), 7.83 (d,J = 8.8, 1H), 7.56 – 7.50 (m, 2H), 7.49 – 7.41 (m,3H), 4.11 (s, 3H), 2.65 (s, 3H).13C ...

Embodiment 2

[0029]Example 2: 2-(3,4-Dimethylphenyl)-8-methyl-1,3-dioxo-2-,3-dihydro-1H-pyrrolo[3,4-c]quine Methyl phthaloline-4-carboxylate

[0030]

[0031]The synthesis method is the same as in Example 1, in which only the raw material N-phenylmaleimide is replaced with N-(3.4-dimethylphenyl)maleimide to obtain a pure white solid product, which is 2-( 3,4-Dimethylphenyl)-8-methyl-1,3-dioxo-2-,3-dihydro-1H-pyrrolo[3,4-c]quinoline-4-carboxylic acid methyl The yield of ester is 53%.

[0032]The NMR data of the compound are as follows:1H NMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 8.24 (d,J = 8.8 Hz, 1H), 7.83 (d,J = 8.8, 1H), 7.28 (d,J = 8.0 Hz, 1H), 7.21 (s,1H), 7.17 (d,J= 8.0 Hz, 1H), 4.12 (s, 3H), 2.66 (s, 3H), 2.32 (s, 6H).13CNMR (151 MHz, CDCl3) δ 166.7, 164.8, 164.8, 149.6, 144.5, 142.5, 137.8, 137.4, 136.0, 135.7, 130.3, 130.2, 128.5, 127.6, 124.1, 123.7, 122.4, 121.3, 53.5, 22.2, 19.9, 19.5.

Embodiment 3

[0033]Example 3: 8-Methyl-1,3-dioxo-2-(p-tolyl)-2,3-dihydro-1H-pyrrolo[3,4-c]quinoline-4-carboxylic acid methyl ester

[0034]

[0035]The synthesis method is the same as in Example 1, wherein only the raw material N-phenylmaleimide is replaced with N-(4-methylphenyl)maleimide. A white solid pure product is obtained, which is 8-methyl-1,3-dioxo-2-(3,4-dimethylphenyl)-2,3-dihydro-1H-pyrrolo[3,4- c] Quinoline-4-carboxylic acid methyl ester, the yield is 50%.

[0036]The NMR data of the compound are as follows:1H NMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 8.24 (d,J = 8.8 Hz, 1H), 7.83 (d,J = 8.8 Hz, 1H), 7.34 (s, 4H), 4.12 (s, 3H), 2.66 (s, 3H), 2.43 (s, 3H).13C NMR (151 MHz, CDCl3) δ 166.8, 164.9, 164.7, 159.5, 149.6, 144.5, 142.5, 136.0, 135.7, 130.2, 128.0, 123.7, 123.6, 122.3, 121.3, 114.5, 55.5, 53.5, 22.2.

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Abstract

The invention provides a synthesis method of pyrrolo [3, 4-c] quinoline 1, 3-diketone compounds, which comprises the following steps: in an organic solvent, by using an Naryl glycine derivative and amaleimide derivative as raw materials, carrying out blue light irradiation reaction at room temperature for 8-12 hours under the actions of an oxidant and a photosensitizer; and after the reaction isfinished, carrying out column chromatography separation to obtain a target product. The method has the advantages of cheap and easily available reaction reagents, small photosensitizer dosage, short reaction steps, mild synthesis conditions, high reaction yield, good product purity, simple and convenient post-treatment, effective reduction of the industrial production cost, and suitableness for industrial production.

Description

Technical field[0001]The invention relates to a method for synthesizing pyrrolo[3,4-c]quinoline-1,3-dione compounds, and belongs to the technical field of organic compound synthesis.Background technique[0002]Pyrrolo[3,4,c]quinoline-1,3-dione compounds are a kind of nitrogen-containing heterocyclic compounds which are widely distributed in nature and have biological activity. Such compounds have a wide range of applications. It is generally believed that these compounds are effective cardioprotective agents, neuroprotective agents, and are expected to be used as anti-arthritis drugs, as well as inhibitors of terminal shearing enzymes in the process of apoptosis, and for the treatment and prevention of hepatitis C virus infection Wait. At the same time as an important organic synthesis intermediate, used to prepare some natural products and related structures.[0003]The structural formula of pyrrolo[3,4-c]quinoline-1,3-dione compounds is as follows:[0004][0005]Where R1Is a hydrocarbon ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/55
Inventor 霍聪德张永新
Owner NORTHWEST NORMAL UNIVERSITY