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Isoindolinone compound containing eneyne structure and synthetic method thereof

A technology of isoindolinone and compound, which is applied in the field of isoindolinone compound and its preparation, can solve the problems of high price and limited application of iodide, and achieve the effects of simple operation, high reaction yield and environmental protection

Inactive Publication Date: 2010-06-23
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] In this reaction literature, iodides are mostly used, and because iodides are expensive, the application of this method in industry is limited.

Method used

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  • Isoindolinone compound containing eneyne structure and synthetic method thereof
  • Isoindolinone compound containing eneyne structure and synthetic method thereof
  • Isoindolinone compound containing eneyne structure and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1: Preparation of (Z)-3-(3-phenylprop-2-ynylmethine)isoindol-1-one

[0063] (Z)-3-(3-phenylprop-2-ynylmethine)isoindol-1-ketone adopts the following steps: 1. add 22.5 grams of (Z)-3- Bromomethylene isoindol-1-one, 10.2 g of phenylacetylene, 0.70 g of dichlorobis(triphenylphosphine)palladium, 0.19 g of cuprous iodide, and 90 ml of triethylamine were heated to 100°C under reflux. Use thin layer chromatography to track the reaction until the reaction raw material (Z)-3-bromomethyleneisoindol-1-one disappears; ②After the reaction is completed, filter with diatomaceous earth, and use a rotary evaporator to remove the solvent to obtain a crude product ; ③The crude product is purified by column chromatography (petroleum ether: ethyl acetate=6: 1) to obtain 22.3 grams of (Z)-3-(3-phenylprop-2-ynylmethine) isoindole- 1-Kone, 91% yield. Melting point: 204-206°C.

[0064] IR(KBr, cm -1 ): 3441, 3168, 1696, 1631, 1590, 1492, 1395, 918, 746. 1 H NMR (CDCl 3 , 500MHz):...

Embodiment 2

[0068] Example 2: Preparation of (Z)-3-(3-(4-fluorophenyl)prop-2-ynylmethine)isoindol-1-one

[0069] (Z)-3-(3-(4-fluorophenyl) prop-2-ynylmethine) isoindol-1-ketone adopts the following steps: 1. add 22.5 grams ( Z)-3-bromomethyleneisoindol-1-one, 14.4 grams of p-fluorophenylacetylene, 1.4 grams of dichlorobis(triphenylphosphine) palladium, 0.76 grams of cuprous iodide, 90 milliliters of triethylamine, Heat to reflux at 100°C. Track the reaction with thin-layer chromatography until the reaction raw material (Z)-3-bromomethyleneisoindol-1-one disappears; ②After the reaction, filter the system with diatomaceous earth, and remove the solvent with a rotary evaporator Obtain crude product; ③ crude product is purified with column chromatography (petroleum ether: ethyl acetate=6: 1), obtains 23.7 grams of (Z)-3-(3-(4-fluorophenyl) prop-2-ynyl Methylene) isoindol-1-one, the yield is 90%. Melting point: 231-233°C. IR(KBr, cm -1 ): 3448, 3183, 3056, 1702, 1638, 1595, 1506, 1470, 14...

Embodiment 3

[0074] Example 3: Preparation of (Z)-3-(3-(4-pentylphenyl)prop-2-ynylmethine)isoindol-1-one

[0075] (Z)-3-(3-(4-pentylphenyl) prop-2-ynylmethine) isoindol-1-one adopts the following steps: 1. add 22.5 grams of (Z)-3-Bromomethyleneisoindol-1-one, 24.1 g p-pentylphenylacetylene, 2.8 g dichlorobis(triphenylphosphine)palladium, 1.3 g cuprous iodide, 90 ml triethyl Amine, heated to reflux at 100°C. Track the reaction with thin-layer chromatography until the reaction raw material (Z)-3-bromomethyleneisoindol-1-one disappears; ②After the reaction, filter the system with diatomaceous earth, and remove the solvent with a rotary evaporator Obtain crude product; 3. crude product is purified by column chromatography (petroleum ether: ethyl acetate=6: 1), obtains 28.7 grams of (Z)-3-(3-(4-pentylphenyl) prop-2-yne methine) isoindol-1-one with a yield of 91%. Melting point: 171-173°C.

[0076] IR(KBr, cm -1 ): 3443, 3160, 3057, 2950, ​​2863, 2185, 1702, 1639, 1603, 1507, 1396, 1136, 94...

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Abstract

The invention relates to an isoindolinone compound containing an eneyne structure and a synthetic method thereof. The compound has the structural formula that: a specific preparation method of the compound comprises the following steps: the isoindolinone and substituted aryne are dissolved in triethylamine according to the molar ratio of 1: (1.0-2.0), dichloro (triphenylphosphine) palladium and cuprous iodide are added in catalyst amount and mixed for reaction till the raw materials are disappeared, and the isoindolinone compound containing the eneyne structure is obtained through filtration, solvent removal and purification after the reaction. The isoindolinone compound containing the eneyne structure is a significant active skeleton of drug molecules and an organic synthetic intermediate, plays an important role in pharmaceutical chemistry and has potential physiological activity. The method has easy availability of raw materials, high reaction yield and wide application range of substrates. The conventional solvent is used in reaction, the operation is simple, the condition is mild, the reaction is environment-friendly, the reaction yield can reach up to 93%, and the method is particularly applicable to industrial production.

Description

technical field [0001] The invention relates to an isoindolinone compound containing an enyne structure and a preparation method thereof. Background technique [0002] Nitrogen-containing heterocycle is a very common pharmacophore in the field of drug research, which has antibacterial, antiviral, antitumor and other physiological activities, and is one of the important goals of small molecule drug development today. In 2007, all of the top 25 brand-name drugs in global sales had nitrogen-containing heterocyclic skeletons. As a common structural unit in nitrogen-containing heterocycles, isoindolinone has good pharmaceutical activity and has been used in anti-degenerative neurological diseases, receptor antagonists or agonists, and enzyme inhibitors. For example, the newly developed anti-anxiety drugs Pazinaclone and Pagoclone, as well as the diuretic and antihypertensive drug Chlortalidone, all contain such skeletons. In addition, isoindolinone compounds are also the core s...

Claims

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Application Information

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IPC IPC(8): C07D209/46
Inventor 许斌王成明翁飞高明春樊婷
Owner SHANGHAI UNIV
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