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A catalytic preparation of pyrano[2,3- b ]Indol-2-one compound method

A technology for catalytic preparation and ketone compounds, applied in chemical instruments and methods, chemical/physical processes, organic compounds/hydrides/coordination complex catalysts, etc. complex problems, to achieve the effect of short reaction time, simple and easy-to-obtain raw materials, and low reaction cost

Active Publication Date: 2022-02-25
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method 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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  • A catalytic preparation of pyrano[2,3- <i>b</i> ]Indol-2-one compound method
  • A catalytic preparation of pyrano[2,3- <i>b</i> ]Indol-2-one compound method
  • A catalytic preparation of pyrano[2,3- <i>b</i> ]Indol-2-one compound method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment one: catalyst [(Me 3 Si) 2 N] 3 La( m -Cl)Li(THF) 3 Synthesis

[0035] 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%.

[0036] Other catalysts can refer to the preparation method of Example 1.

Embodiment 2

[0037]Embodiment two: [(Me 3 Si) 2 N] 3 La( m -Cl)Li(THF) 3 catalytic N -Preparation of pyrano[2,3- b ]indol-2-one compounds

[0038] 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), followed by adding diethyl phosphite (37 μL, 0.29 mmol), N -Ethyl-5-fluoroisatin (56.0 mg, 0.29 mmol), toluene (0.4 mL), stirred at room temperature for 10 minutes, then added 2,3-diphenylcyclopropenone (50 mg, 0.24 mmol), toluene ( 0.6 mL), stirred at 110°C for 1.5 hours, added water to terminate the reaction, extracted three times with ethyl acetate, dried the extract with anhydrous sodium sulfate, filtered, removed the solvent under reduced pressure, and finally passed through silica gel column flash column chromatography (eluent : ethyl acetate:petroleum ether=1:10) to obtain a yellow solid product with a yield of 82%.

[0039] The theoretical molecular formula of the obtained product and the main ...

Embodiment 3

[0042] 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

[0043] 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), followed by adding diethyl phosphite (37 μL, 0.29 mmol), N -Ethyl-5-chloroisatin (60.6 mg, 0.29 mmol), toluene (0.4 mL), stirred at room temperature for 10 minutes, then added 2,3-diphenylcyclopropenone (50 mg, 0.24 mmol), toluene ( 0.6 mL), stirred at 110°C for 1.5 hours, added water to terminate the reaction, extracted three times with ethyl acetate, dried the extract with anhydrous sodium sulfate, filtered, removed the solvent under reduced pressure, and finally passed through silica gel column flash column chromatography (eluent : ethyl acetate:petroleum ether=1:10) to obtain a yellow solid product with a yield of 95%.

[0044] The theoretical molecular formula of the obtained product and the ma...

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Abstract

The invention discloses a method for catalytically preparing pyrano[2,3- b ] the method of indole 2 ketone compound, with silicon amino rare earth compound [(Me 3 Si) 2 N] 3 Ln( m -Cl)Li(THF) 3 As a catalyst, the product is prepared by catalyzing the one-pot reaction of substituted isatin, phosphite and cyclopropenone; in the catalyst, (Me 3 Si) 2 N represents trimethylsilylamino, Ln represents positive trivalent rare earth metal ions, selected from one of lanthanum, neodymium, samarium, erbium or ytterbium; m ‑represents a bridge; THF represents tetrahydrofuran. In this method, the catalyst synthesis method is simple, the reaction raw materials are simple and easy to obtain, the substrate has a wide range of applications, the one-pot reaction method has high efficiency, the reaction is simple and efficient, and the yield of the target product is as high as 95%.

Description

technical field [0001] The invention belongs to the technical field of preparation of fused heterocycles, in particular to a pyrano[2,3- b ] Catalytic preparation of indol-2-one compounds. Background technique [0002] 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-efficiency synthesis technology of ]indol-2-one skeleton has important theoretical and practical significance. [0003] In the prior art, reported pyrano[2,3- b ] There are very few synthetic routes for the indol-2-one skeleton, and there are mainly three methods. One, Michaelis acid derivatives and N-(2-iodophenyl) propynylamide are synthesized through a three-step reaction under certain conditions (referring to A. Arcadi, S. Cacchi, F. Marinelli, P. Pace, Synlett , 1993, 743.); Second, the synthesis of 2-hydroxy-3-acetylindole derivative...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052B01J31/18
CPCC07D491/052B01J31/1805B01J2531/37B01J2531/38B01J2531/0213
Inventor 陈启发徐凡滕月
Owner SUZHOU UNIV