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Preparation method of isatin derivatives

A technology of derivatives and isatin, which is applied in the field of preparation of isatin derivatives, achieves the effect of low cost and simple and easy process operation

Active Publication Date: 2017-09-08
NINGBO UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

[0010] After painstaking research, the inventor proposed a new method for preparing isatin derivatives by oxidation of substituted 2-indolinone compounds, which has not been reported

Method used

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  • Preparation method of isatin derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-12

[0025] Embodiment 1-12 Reaction condition optimization

[0026] Isatin (I-1) was prepared by reacting 2-indolinone (1a) with tert-butyl nitrite (2a) as the raw material. The influence of different reaction conditions on the reaction was explored, and a representative implementation was selected. Example 1-12, the results are shown in Table 1:

[0027]

[0028] Table I:

[0029] Example Auxiliary (equivalent) solvent Isolated yield 1 TBHP(2) THF 0 2 DTBP(2) THF 0 3 t-BuONO(2) THF 77 4 K 2 S 2 o 8 (2)

THF 5 5 t-BuONO(1.2) THF 61 6 t-BuONO(3) THF 76 7 a

t-BuONO(2) THF 28 8 b

t-BuONO(2) THF 0 9 t-BuONO(2) 1,4-dioxane 12 10 t-BuONO(2) EtOAc 75 11 t-BuONO(2) toluene 5 12 c

t-BuONO(2) THF 70

[0030] Taking Example 3 as an example, its specific operation is as follows: add 2-indolinone (1a, 0.3mmol), tert-butyl nitrite (t-BuONO, 2a, 0.6mm...

Embodiment 7

[0032] In embodiment 7, "a" represents that reaction is carried out under air atmosphere (1atm) condition;

Embodiment 8

[0033] "b" in Example 8 represents that the reaction is carried out under nitrogen atmosphere conditions;

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Abstract

The invention discloses a novel method for synthesizing isatin derivatives. According to the method, a catalytic oxidation system of tert-butyl nitrite / O2 is adopted without using metal reagents, reaction is performed at room temperature under normal pressure, and isatin derivatives are obtained with high yield and high purity. The method has the advantages of simple technical operation process and low cost.

Description

technical field [0001] The invention relates to a preparation method of isatin derivatives, in particular to a method for preparing isatin derivatives with simple process and environment-friendly method using 2-indolinone derivatives as raw materials. Background technique [0002] Since 1841, Erdmann and Laurent have independently obtained a molecule called C by oxidation of indigo. 8 h 6 NO 2 and named it indoledione (isatin, i.e. isatin), and until Kolbe finally determined its structure, the chemical properties and uses of indoledione were gradually recognized by people. Today, it has been found that compounds with indoledione skeletons are widely used in dyes, antibiotics, and anticancer drugs. Therefore, the synthesis of compounds containing this type of skeleton has attracted more and more attention from organic synthetic chemists. [0003] In 1841, Erdmann and Laurent obtained indoledione independently through experiments using indigo as the starting material under...

Claims

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Application Information

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IPC IPC(8): C07D209/38
CPCC07D209/38
Inventor 黄依铃魏文廷应炜炜吴益伍科玮曹奕琦汪依宁朱立伟
Owner NINGBO UNIV
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