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A kind of preparation method of [1,2,4]oxadiazinoindolin-3-one derivative

A technology of derivatives and indole, applied in the field of preparation of [1,2,4]oxadiazinoindolin-3-one derivatives, which can solve the problems of low economic efficiency, complex oxidation rearrangement, and cumbersome steps and other problems, to achieve the effects of strong reaction specificity, wide substrate range, and easy post-treatment

Active Publication Date: 2022-06-07
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional synthetic methods of fused-ring fused-ring indolin-3-ones usually involve complex biosynthesis and oxidative rearrangement of indole alkaloids, which are cumbersome and not economical

Method used

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  • A kind of preparation method of [1,2,4]oxadiazinoindolin-3-one derivative
  • A kind of preparation method of [1,2,4]oxadiazinoindolin-3-one derivative
  • A kind of preparation method of [1,2,4]oxadiazinoindolin-3-one derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of product 1:

[0031]

[0032] Add 0.20mmol of 2-(phenylethynyl)nitrobenzene and 0.01mmol of gold trichloride to a reaction tube containing 0.50mL of toluene, react at room temperature for 3h, and then add 0.50mmol of N-(benzyloxy)-2 -Bromo-2-methylpropionamide, 1.0 mmol sodium carbonate, 1.0 mL hexafluoroisopropanol, react at room temperature for 12 h. The reaction solution was extracted with water / dichloromethane (25mL / 25mL), the organic phase was collected and concentrated, and purified by column chromatography to obtain 67.3 mg of the target product with a yield of 81%. The structure of the compound was characterized as follows: 1 H NMR (400MHz, CDCl 3 )δ7.77(d,J=8.1Hz,1H),7.65(t,J=7.7Hz.,1H),7.52–7.44(m,4H),7.40–7.28(m,7H),7.11(t, J=7.5Hz, 1H), 5.01 (d, J=8.8Hz, 1H), 4.86 (d, J=8.8Hz, 1H), 1.59 (d, J=4.4Hz, 6H). 13 C NMR (100MHz, CDCl 3 )δ189.7,168.9,158.6,137.6,133.9,133.8,129.9,129.4,128.8,128.6,128.3,127.7,125.4,122.8,119.1,113.7,87.0,84.0,77...

Embodiment 2

[0034] Preparation of product 1:

[0035] 0.10 mmol 2-(phenylethynyl) nitrobenzene, 0.01 mmol palladium dichloride, 0.10 mmol N-(benzyloxy)-2-bromo-2-methylpropionamide, 0.20 mmol sodium carbonate were added to a mixture containing 2.0 In a reaction tube containing hexafluoroisopropanol, the reaction was carried out at 60 °C for 12 h, the reaction solution was extracted with water / dichloromethane (25 mL / 25 mL), the organic phase was collected and concentrated, and after purification by column chromatography, the yield was 45%. The target product (structural characterization is the same as in Example 1).

Embodiment 3

[0037] Preparation of product 1:

[0038] 0.10 mmol 2-(phenylethynyl) nitrobenzene, 0.01 mmol palladium acetate, 0.10 mmol N-(benzyloxy)-2-bromo-2-methylpropionamide, 0.20 mmol sodium carbonate were added to a mixture containing 2.0 mL In a reaction tube of fluoroisopropanol, react at 60°C for 12h, extract the reaction solution with water / dichloromethane (25mL / 25mL), collect the organic phase and concentrate, and purify by column chromatography to obtain the target product with a yield of 41%. (Structural characterization is the same as in Example 1).

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Abstract

The invention discloses a preparation method of [1,2,4]oxadiazinoindoline-3-one derivatives, comprising the following steps: (1) preparing an o-nitrophenylacetylene compound, a catalyst and a first organic After the solvents are mixed, react at room temperature for 3-6h; (2) add α-halogenated hydroxamate compound, sodium carbonate and hexafluoroisopropanol to the material obtained in step (1), and react for 10 h at room temperature ‑12h; or mix o-nitrophenylacetylene compound, catalyst, α‑halogenated hydroxamate compound, sodium carbonate and hexafluoroisopropanol and react at 55‑65°C for 10‑12h. The invention can synthesize [1,2,4]oxadiazinoindoline-3-one derivatives with various substituents which are difficult to synthesize by other methods, and has far-reaching significance from the perspective of organic chemistry.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of a [1,2,4]oxadiazinoindolin-3-one derivative. Background technique [0002] Fused-ring indolin-3-ones occupy an important position in the indole alkaloid family because of their fascinating molecular structures and potential biological activities. Some fused-ring indolin-3-ones have been found to have a variety of Biological activity and fluorescence properties have potential application value in drug molecule synthesis and luminescent material development; on the other hand, [1,2,4]oxadiazine derivatives have important application value in herbicide, diuresis, and anti-inflammatory. Therefore, the study of [1,2,4]oxadiazinyl[2,3-a]indole-2,10(3H)-dione derivatives and their synthesis methods is of great value, and has been widely studied by researchers in related fields. focus on. [0003] Traditional synthetic methods of fused-ring and fused-r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04C07D498/10
CPCC07D498/04C07D498/10
Inventor 崔秀灵黄浪
Owner HUAQIAO UNIVERSITY
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