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Method for preparing N-substituted isatin derivatives

A derivative, isatin technology, applied in the field of novel preparation, can solve the problems of large hidden dangers in environmental protection, unobtainable raw materials, and large environmental pollution, and achieve the effects of less three wastes, cheap raw materials, and environmental friendliness

Active Publication Date: 2019-05-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In these methods for synthesizing isatin, transition metal catalysts or stoichiometric chemical oxidants are mostly used. Some materials such as phosphorus oxychloride have high toxicity and environmental protection hazards. The raw materials of aniline diazoacetate are not easy to obtain and are environmentally friendly. High pollution, which limits its application

Method used

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  • Method for preparing N-substituted isatin derivatives
  • Method for preparing N-substituted isatin derivatives
  • Method for preparing N-substituted isatin derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 1-methylindoline-2,3-dione (I-a)

[0037] Add raw material II N-methyl-2-(methyl(phenyl)amino)acetamide (1.78g, 10mmol) to a 50mL single-necked bottle, the acid is trifluoroacetic acid (0.91g, 8mmol), at 60°C in 10ml acetonitrile React 10h under 1L of oxygen. After the reaction, it was cooled, poured into 100 mL of water, filtered, washed and dried to obtain 1.50 g of solid product with a yield of 93.1% and a melting point of 130.0-133.0°C.

Embodiment 2

[0038] Example 2 1-Ethyl-5-methylindoline-2,3-dione (I-b)

[0039] Add raw material II N-ethyl-N-(p-tolyl)glycine ethyl ester (2.21g, 10mmol) to a 50mL single-necked bottle, the acid is trichloroacetic acid (3.27g, 20mmol), in 50ml anisole at 80°C Pass 1L of oxygen to react for 8h. After the reaction, it was cooled, poured into 100 mL of water, filtered, washed and dried to obtain 1.62 g of solid product with a yield of 85.6% and a melting point of 157.2-158.5°C.

Embodiment 3

[0040] Example 3 1-isopropyl-5-fluoroindoline-2,3-dione (I-c)

[0041] Add raw material II N-(4-fluorophenyl)-N-isopropylglycine isopropyl ester (2.53g, 10mmol) in a 50mL single-necked bottle, the acid is 2-fluoropropionic acid (4.92g, 30mmol), at 150 React in 120ml DMF at ℃ for 4h under the atmosphere. After the reaction, it was cooled, poured into 100 mL of water, filtered, washed and dried to obtain 1.48 g of solid product with a yield of 71.4% and a melting point of 160.7-162.5°C.

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Abstract

A method for preparing isatin derivatives from substituted aniline is disclosed. The method includes subjecting substituted aniline shown as a formula II as a raw material to self-cyclization under anacid catalytic oxidation condition to prepare the isatin derivative with a high yield. The method is simple in process, simple to operate, mild in reaction condition, and short in reaction period. The derivatives are critical intermediates, and raw materials are cheap. The method is environmentally friendly, avoiding heavy metal pollution and use of a catalyst, and generating little 'three wastes'. The method is high in product yield and purity and is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a novel preparation method for preparing isatin derivatives by self-cyclization of single molecules. (2) Background technology [0002] Isatin, also known as indoloquinone, is an important natural product widely distributed in animals, plants and human body. Isatin is found in the metabolites of plants such as the Acanthaceae plant Isatis indigo and the cruciferous plant and microorganisms; the symbiotic marine bacteria of the long arm shrimp can also produce isatin, which has a strong inhibitory effect on pathogenic fungi Function: It is highly distributed in human organs and body fluids, especially in the hippocampus and other parts of the brain. [0003] Isatin and its derivatives have a variety of biological activities, and their activities in antitumor, antiviral, neuroprotective and other aspects are very meaningful. Its 1, 2, 3 positions and benzene ring can undergo various types of chemical reactions, which provid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/38
Inventor 李坚军周嘉第陈永健兰凯苏为科
Owner ZHEJIANG UNIV OF TECH
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