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Application of silylamino rare earth compound in catalysis of reaction of isatin compound and cyclopropenone compound

A technology of rare earth compounds and cyclopropenone, applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, chemical instruments and methods, etc. The steps are cumbersome and other problems, to achieve the effect of short reaction time, low reaction cost, and simple and easy-to-obtain raw materials

Pending Publication Date: 2021-06-15
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Existing methods can synthesize pyrano[2,3- b ] indol-2-one compounds, but there are some defects, such as: low yield, complex synthesis steps, complex substrate structure, need to use noble metal catalysts, etc.

Method used

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  • Application of silylamino rare earth compound in catalysis of reaction of isatin compound and cyclopropenone compound
  • Application of silylamino rare earth compound in catalysis of reaction of isatin compound and cyclopropenone compound
  • Application of silylamino rare earth compound in catalysis of reaction of isatin compound and cyclopropenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment one: catalyst [(Me 3 Si) 2 N] 3 La( m -Cl)Li(THF) 3 Synthesis

[0036] At -10°C, the n -BuLi in hexane solution (60 mmol, 2.52 M) was added dropwise to the (Me 3 Si) 2 NH (60mmol) in a 100 mL Schlenk reaction flask and reacted at room temperature for 30 minutes. The above reaction solution was added to anhydrous LaCl 3 (20 mmol) in THF (30 mL) and stirred overnight at room temperature. The solvent was removed under reduced pressure, and the obtained solid powder was extracted with hot toluene to remove LiCl, concentrated, placed at 0°C, and a large number of crystals were precipitated, which was the desired lanthanum siliconamide compound, with a yield of 85%.

[0037] Other catalysts can refer to the preparation method of Example 1.

Embodiment 2

[0038] Embodiment two: [(Me 3 Si) 2 N] 3 Yb( m -Cl)Li(THF) 3 catalytic N Preparation of pyrano[2,3- b ]indol-2-one compounds

[0039] In the reaction flask treated with dehydration and deoxygenation, weigh [(Me 3 Si) 2 N] 3 Yb( m -Cl)Li(THF) 3 (43.8 mg, 0.048 mmol), diethyl phosphite (37 μL, 0.29 mmol), N-Ethyl isatin (50.7 mg, 0.29 mmol), mixed with conventional stirring for 30 minutes, then added solvent (1.0 mL), 2,3-diphenylcyclopropenone (50 mg, 0.24 mmol), stirred at 50 °C After 1.5 hours, add water to terminate the reaction, extract three times with ethyl acetate, dry the extract with anhydrous sodium sulfate, filter, remove the solvent under reduced pressure, and finally perform flash column chromatography on a silica gel column (eluent: ethyl acetate:petroleum ether=1 : 10) Obtain a yellow solid product; the theoretical molecular formula and main NMR test data of the obtained product are as follows, and it can be seen from the analysis that the actual synt...

Embodiment 3

[0045] Embodiment three: [(Me 3 Si) 2 N] 3 La( m -Cl)Li(THF) 3 catalytic N Preparation of pyrano[2,3- b ]indol-2-one compounds

[0046] In the reaction flask treated with dehydration and deoxygenation, weigh [(Me 3 Si) 2 N] 3 La( m -Cl)Li(THF) 3 (42.2 mg, 0.048 mmol), diethyl phosphite (37 μL, 0.29 mmol), N -Ethyl isatin (50.7 mg, 0.29 mmol), mixed with conventional stirring for 30 minutes, then added toluene (1.0 mL), 2,3-diphenylcyclopropenone (50 mg, 0.24 mmol), stirred at 50°C After 1.5 hours, add water to terminate the reaction, extract three times with ethyl acetate, dry the extract with anhydrous sodium sulfate, filter, remove the solvent under reduced pressure, and finally perform flash column chromatography on a silica gel column (eluent: ethyl acetate:petroleum ether=1 :10) to obtain a yellow solid product with a yield of 82%.

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Abstract

The invention discloses application of ansilylamino rare earth compound in catalysis of a reaction of an isatin compound and a cyclopropenone compound. The silylamino rare earth compound is [(Me<3>Si)<2>N]<3>Ln(m-Cl)Li(THF)<3>. In the presence of phosphite, a reaction of the isatin compound and cyclopropenone is catalyzed by thesilylaminorare earth compound, so a method, which is simple in raw material source, simple in step, mild in reaction conditions, high in activity and good in universality, for synthesizing the pyrano[2,3-b]indol-2-one compound,is realized.

Description

technical field [0001] The invention belongs to the technical field of preparation of condensed heterocycles, and in particular relates to the application of silicon amino rare earth compounds in catalyzing the reaction of isatin compounds and cyclopropenone compounds. Background technique [0002] pyrano[2,3- b ]Indol-2-one skeleton contains pyran and indole, which is one of the most important structural units in medicinal chemistry. There are different preparations of pyrano[2,3- b ]Indol-2-one skeleton method, such as: [0003] [0004] Existing methods can synthesize pyrano[2,3- b ] indol-2-one compounds, but there are some defects, such as: low yield, complex steps, complex substrate structure, need to use noble metal catalysts, and so on. pyrano[2,3- b ]Indol-2-one skeleton is a very important structural unit, which widely exists in natural products and drug molecules, and has certain biological activities. Therefore, the study of pyrano[2,3- b The high-effici...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/18C07D491/052
CPCB01J31/1805C07D491/052B01J2531/37B01J2531/38B01J2531/0213Y02P20/584
Inventor 姚志刚陈启发徐凡
Owner SUZHOU UNIV
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