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1,3-disubstituted indoline derivative and preparation method thereof

A technology for indoline and derivatives, applied in the field of indoline derivatives and their preparation, can solve problems such as high temperature, harsh reaction conditions, and long reaction time, and achieve the effects of simple raw materials, fast reaction speed, and wide sources

Inactive Publication Date: 2020-02-18
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although the above method can synthesize many indoline derivatives, there are still many shortcomings, such as the need for transition metal catalysis, and the reaction conditions are relatively harsh, requiring high temperature and long reaction time

Method used

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  • 1,3-disubstituted indoline derivative and preparation method thereof
  • 1,3-disubstituted indoline derivative and preparation method thereof
  • 1,3-disubstituted indoline derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Synthesis of 1,3-dimethylindoline from 2-iodoaniline

[0073]

[0074] 2-iodoaniline (2.19 g), potassium carbonate (2.76 g), dimethyl sulfoxide (DMSO, 50 ml) were added to a round bottom flask, and methyl iodide (CH 3 1, 1.42 grams), the dropwise addition was completed, and the ice bath was removed, and the resulting mixed system was warmed up to room temperature, and continued to stir for 12 hours; afterward, continue to drip allyl bromide (1.21 grams) under the ice bath, after the dropwise addition, room temperature reaction After 16 hours, add deionized water (50 ml) to quench the reaction, use 50 ml of ether to extract 3 times, combine the organic phases, and remove the solvent under reduced pressure on a rotary evaporator to obtain N-methyl-N-allyl- 2-iodoaniline crude product (2.42 grams), this product can carry out next step reaction without further purification;

[0075] SmI 2 (0.1 mol / L tetrahydrofuran solution, 120 ml) was added to the reaction...

Embodiment 2

[0079] Embodiment 2: Starting from 2-iodoaniline, synthesis of N-acetyl-3-methylindoline

[0080]

[0081] 2-iodoaniline (2.19 g), potassium carbonate (2.76 g), dimethyl sulfoxide (DMSO, 50 ml) were added to a round-bottomed flask, and acetyl chloride (AcCl, 785 mg) was slowly added dropwise under ice-cooling. After the addition was complete, the ice bath was removed, and the resulting mixed system was raised to room temperature, and continued to stir for 12 hours; after that, allyl bromide (1.21 g) was added dropwise under the ice bath. Water (50 milliliters) quenches reaction, uses 50 milliliters of diethyl ether to extract 3 times, combines organic phase, removes solvent under reduced pressure on rotary evaporator and obtains N-acetyl-N-allyl-2-iodoaniline (2.77 grams ) crude product, this product can carry out next step reaction without further purification;

[0082] SmI 2 (0.1 mol / liter tetrahydrofuran solution, 120 milliliters) was added in the reaction tube, and tr...

Embodiment 3

[0086] Example 3: Synthesis of N-acetyl-3,5-dimethylindoline from 2-iodoaniline

[0087]

[0088]2-iodo-4-methylaniline (2.19 g), potassium carbonate (2.76 g), dimethyl sulfoxide (DMSO, 50 ml) were added to a round bottom flask, and acetyl chloride (AcCl, 785 mg), the dropwise addition was completed, and the ice bath was removed, and the resulting mixed system was raised to room temperature, and continued to stir for 12 hours; after that, continued dropwise addition of allyl bromide (1.21 g) under the ice bath, after the dropwise addition, room temperature was reacted for 16 hours Finally, add deionized water (50 ml) to quench the reaction, use 50 ml of ether to extract 3 times, combine the organic phases, and remove the solvent under reduced pressure on a rotary evaporator to obtain N-acetyl-N-allyl-2- Iodo-4-methylaniline (3.03 grams) crude product, this product can carry out next step reaction without further purification;

[0089] SmI 2 (0.1 mol / L tetrahydrofuran solu...

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Abstract

The invention relates to a 1,3-disubstituted indoline derivative and a preparation method thereof, and belongs to the field of organic compound synthesis. The preparation method comprises following steps: step one, according to a mole ratio of (1-3): (2-10): 1: (3-8), in the absence of oxygen, dissolving SmI2, tertiary amine, allyl substituted 2-iodo aromatic amine, and deionized water by tetrahydrofuran to obtain a mixed system A; step two, making the mixed system carry out reactions for 0.5 to 20 minutes at a temperature of 20 to 30 DEG C, and removing the organic solvent and byproducts in the obtained reaction liquid to obtain the 1,3-disubstituted indoline derivative. Water is used as a proton donor, the reactions are triggered by samarium iodide, and under the catalytic action, cyclization of free radicals happens in tetrahydrofuran. The target product is obtained under mild conditions. The reaction speed is quick, the conditions are mild, and the obtained 1,3-disubstituted indoline derivative can be widely used in fields such as medicine, pesticide, and the like.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and specifically relates to a 1,3-disubstituted indoline derivative and a preparation method thereof. Background technique [0002] Indoline, also known as 2,3-dihydroindole, is a product obtained by hydrogenation of indole at the 2 and 3 positions, and is an aromatic bicyclic organic heterocyclic compound. As a characteristic structural fragment, the indoline skeleton structure widely exists in biologically active natural products and drug molecules, and plays an extremely important role in the fields of anti-inflammation, anti-microbial, anti-Plasmodium falciparum and anti-cancer. At present, there are some drugs containing indoline skeletons on the market, such as: Pentopril (Pentopril), an effective drug for the treatment of hypertension, peroxidase proliferator-activated receptor (PPARα / γ) and liver X receptor modulators, etc. For details, see the literature "J.Clin.Pharm.1986,26,1...

Claims

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Application Information

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IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 解攀薛成石三山李瑶
Owner SHAANXI UNIV OF SCI & TECH
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