Synthesis method of (1,1-dicyano-4-oxygen)-hexyl-3-oxindole phosphonite diethyl and its derivatives

A technology of diethyl indole phosphinate and synthesis method is applied in the field of synthesis of diethyl-hexyl-3-oxyindole phosphinate and derivatives thereof, and achieves high reaction yield, simple steps and high reaction efficiency. short time effect

Active Publication Date: 2022-05-27
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, in the synthetic system, the constructed "carbon four center" is still a difficult point in organic synthetic chemistry, and this kind of oxindole derivatives containing phosphonate groups has not been reported yet.

Method used

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  • Synthesis method of (1,1-dicyano-4-oxygen)-hexyl-3-oxindole phosphonite diethyl and its derivatives
  • Synthesis method of (1,1-dicyano-4-oxygen)-hexyl-3-oxindole phosphonite diethyl and its derivatives
  • Synthesis method of (1,1-dicyano-4-oxygen)-hexyl-3-oxindole phosphonite diethyl and its derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0027] A kind of (1,1-dicyano-4-oxo)-hexyl-3-oxyindole phosphonite and its derivative (1,1-dicyano-4-oxo)-hexyl-3 -The synthetic method of oxyindole phosphinate, comprising:

[0028]

[0029] 1.0 mmol (0.147 g) isatin, 1.0 mmol (0.066 g) malononitrile, 1.0 mmol (0.138 g) diethyl phosphite and 0.2 mmol ionic liquid catalyst 1,4-diazabicyclo[2.2.2] were successively mixed Octane acetate was added to a 10ml dry round-bottomed flask, then 1ml of tetrahydrofuran was added as a solvent, heated and stirred at 40°C for 30min, and then 1.0mmol (0.084g) of 1-penten-3-one was added to continue the reaction at 40°C, The reaction was monitored by TLC. After the reaction was completed (1.5h), 10ml of water was added. After cooling, 10ml of ethyl acetate was added for extraction 3 times. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated, and the crude product was separated by column chromatography. Purify, adopt petroleum ether and ethyl acetate as eluent...

Embodiment 2

[0034] A kind of (1,1-dicyano-4-oxo)-hexyl-3-oxyindole phosphonite and its derivative (1,1-dicyano-4-oxo)-hexyl-3 -The synthetic method of dimethyl oxyindole phosphinate, comprising:

[0035]

[0036]1.0 mmol (0.147 g) isatin, 1.0 mmol (0.066 g) malononitrile, 1.0 mmol (0.110 g) dimethyl phosphite and 0.2 mmol ionic liquid catalyst 1,4-diazabicyclo[2.2.2] Octane acetate was added to a 10ml dry round-bottomed flask, then 1ml of tetrahydrofuran was added as a solvent, heated and stirred at 40°C for 30min, and then 1.0mmol (0.084g) of 1-penten-3-one was added to continue the reaction at 40°C, The reaction was monitored by TLC. After the reaction was completed (36h), 10ml of water was added. After cooling, 10ml of ethyl acetate was added for extraction 3 times. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated, and the crude product was separated and purified by column chromatography. , using petroleum ether and ethyl acetate as eluent (in part...

Embodiment 3

[0041] A kind of (1,1-dicyano-4-oxo)-hexyl-3-oxyindole phosphonite and its derivative (1,1-dicyano-4-oxo)-hexyl-3 -The synthetic method of diphenyl oxyindole phosphinate, comprising:

[0042]

[0043] 1.0 mmol (0.147 g) isatin, 1.0 mmol (0.066 g) malononitrile, 1.0 mmol (0.110 g) dimethyl phosphite and 0.2 mmol ionic liquid catalyst 1,4-diazabicyclo[2.2.2] Octane acetate was added to a 10ml dry round-bottomed flask, then 1ml of tetrahydrofuran was added as a solvent, heated and stirred at 40°C for 30min, and then 1.0mmol (0.084g) of 1-penten-3-one was added to continue the reaction at 40°C, The reaction was monitored by TLC. After the reaction was completed (12h), 10 ml of water was added. After cooling, 10 ml of ethyl acetate was added for extraction three times. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated, and the crude product was separated and purified by column chromatography. , using petroleum ether and ethyl acetate as eluent (...

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Abstract

The invention discloses a synthesis method of (1,1-dicyano-4-oxygen)-hexyl-3-oxindole phosphinate diethyl ester and its derivatives. The synthesis method comprises: adding DABCO-based ionic liquid Under catalysis, the first reactant, malononitrile, phosphite, and enone compound are heated and reacted relatively gently in a solvent to prepare the oxindole derivatives containing phosphonate groups. The synthesis method of the present invention has simple steps, is a four-component "one-pot" reaction, can selectively synthesize chain-like indole compounds with phosphonate groups, has short reaction time, and relatively high reaction yield , the ionic liquid catalyst used is cheap and easy to obtain, and it is a novel and efficient four-component reaction.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing (1,1-dicyano-4-oxo)-hexyl-3-oxyindole phosphonite diethyl ester and derivatives thereof. Background technique [0002] Oxidole derivatives are a very important class of nitrogen-containing heterocyclic compounds. They are important skeletons of many natural products and biologically active compounds. The rich and diverse structures of these derivatives, as well as their broad-spectrum biological activities, This class of compounds is in great need of efficient synthetic methods. Moreover, in the synthesis system, the constructed "carbon four-center" is still a difficulty in organic synthesis chemistry, and such oxindole derivatives containing phosphonate groups at the same time have not been reported yet. SUMMARY OF THE INVENTION [0003] In view of the deficiencies in the prior art, the object of the present invention is to prov...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/572
CPCC07F9/5728Y02P20/54
Inventor 徐大振徐一泽王政林胡欣李若璞
Owner NANKAI UNIV
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