Synthesis method of spirooxindole compounds

A synthesis method and spirocyclic indole technology are applied in the field of organic synthesis, can solve problems such as complex synthesis of raw materials, and achieve the effects of simple and safe operation and no catalyst needed.

Active Publication Date: 2018-08-24
INNOVATIVE DRUG RES & DEV CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Green and efficient synthesis methods without transition metal catalysis are only

Method used

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  • Synthesis method of spirooxindole compounds
  • Synthesis method of spirooxindole compounds
  • Synthesis method of spirooxindole compounds

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Experimental program
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Embodiment 1

[0030] In the present embodiment, the reaction formula of the synthetic method of spiro indole compound is as follows:

[0031]

[0032] The raw material 1a (0.2 mmol) was added into the reaction flask, 5.0 mL of dichloromethane was added to dissolve at room temperature, PCC (0.24 mmol) was added, the temperature was raised to 40°C and the reaction was stirred for 5 hours. Then the solvent was removed under reduced pressure, and the purified spiro indole compound 2a was obtained after column chromatography of the crude product, which was a colorless liquid with a purity of >95% and a yield of 85%.

[0033] The obtained product 2a is characterized by nuclear magnetic resonance, such as figure 1 The H spectrum shown and figure 2 The C spectrum shown, the deuterated reagent used for NMR characterization is CDCl 3 .

Embodiment 2

[0035] In the present embodiment, the reaction formula of the synthetic method of spiro indole compound is as follows:

[0036]

[0037] Add raw material 1b (0.2mmol) into the reaction flask, add 4.0mL chloroform to dissolve at room temperature, add PCC (0.40mmol), heat up to 20°C and stir for 12 hours. Then the solvent was removed under reduced pressure, and the purified spiro indole compound 2b was obtained after column chromatography of the crude product, which was a white solid with a purity of >95% and a yield of 87%.

[0038] The obtained product 2b is characterized by nuclear magnetic resonance, such as image 3 The H spectrum shown and Figure 4 The C spectrum shown, the deuterated reagent used for NMR characterization is CDCl 3 .

Embodiment 3

[0040] In the present embodiment, the reaction formula of the synthetic method of spiro indole compound is as follows:

[0041]

[0042] Add raw material 1c (0.2 mmol) into the reaction flask, add 4.0 mL of acetonitrile at room temperature to dissolve, add PCC (0.22 mmol), heat up to 110° C. and stir for 2 hours. Then the solvent was removed under reduced pressure, and the purified spiro indole compound 2c was obtained after column chromatography of the crude product, which was a white solid with a purity of >95% and a yield of 89%.

[0043] The obtained product 2c is characterized by nuclear magnetic resonance, such as Figure 5 The H spectrum shown and Figure 6 The C spectrum shown, the deuterated reagent used for NMR characterization is CDCl 3 .

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Abstract

The invention relates to a synthesis method of spirooxindole compounds. The synthesis method comprises the steps as follows: spirooxindole compounds shown in a formula (I) are subjected to a rearrangement reaction in an organic solvent under the oxidation action of PCC (pyridinium chlorochromate), and spirooxindole compounds shown in a formula (II) are obtained, wherein the reaction temperature is20-120 DEG C, the reaction formula is shown in the description, Ar represents aryl or substituted aryl, and PG represents a protection group. The spirooxindole compounds are obtained through the one-step PCC oxidative rearrangement reaction, and the method has the advantages of simplicity and safety in operation, atom economy and capability of constructing multiple chemical bonds in one step.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing spirocyclic indole compounds. Background technique [0002] Spiral indole compounds are a kind of basic framework for constructing biologically active compounds, and there are many substances containing such structural units in nature. At present, the effective methods for the synthesis of spiro indole compounds mainly include the oxidation / lactonization reaction of indole propionic acid, the tandem Michael ring expansion conversion reaction of oxindolinone, etc. However, the main problems with these reactions are as follows: [0003] The oxidation / lactonization of indolepropionic acid has many problems, such as cumbersome steps, transition metal catalysis, harsh conditions, and low yield; Indole compounds have regioselectivity problems. More importantly, few of these methods involve the direct synthesis of compounds with spirocyclic indole ...

Claims

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Application Information

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IPC IPC(8): C07D491/107
CPCC07D491/107Y02P20/55
Inventor 徐新芳苏涵蔡菊张成邱丽华
Owner INNOVATIVE DRUG RES & DEV CENT
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