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The synthetic method of 2,3-dihydropyrrole ring

A technology of dihydropyrrole ring and synthesis method, applied in the direction of organic chemistry, etc., to achieve the effect of easy-to-obtain raw materials, high yield, and mild conditions

Active Publication Date: 2020-04-07
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still few methods for rapid and efficient synthesis of 2,3-dihydropyrrole rings at room temperature without using metal catalysts, especially the simple operation, and the method reports for the one-step synthesis of 2,3-dihydropyrrole rings and their derivatives are yet to be developed

Method used

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  • The synthetic method of 2,3-dihydropyrrole ring
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  • The synthetic method of 2,3-dihydropyrrole ring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 (α, the synthesis of gamma disubstituted allenic acid ester)

[0035] Add 47.2g of triphenylphosphine and 200ml of ethyl acetate into a 500ml three-necked flask, and stir for 10 minutes. Dissolve 20ml of ethyl bromoacetate in 60ml of ethyl acetate and add it to the reaction solution to form a white precipitate. Continue to stir for 12 hours. Treatment: After filtering, wash with ether and dry with anhydrous sodium sulfate, add 200 methylene chloride to dissolve, add KOH aqueous solution (10gKOH+120ml water), extract the aqueous phase with methylene chloride twice, combine the organic phase with anhydrous sulfuric acid Dry over sodium, and remove the solvent dichloromethane by rotary evaporation to obtain the crude product phosphorus ylide in the first step. Its reaction formula 4 is as follows:

[0036]

[0037] Reaction 4

[0038] Dissolve the above phosphorus ylide product in 25ml of chloroform, heat to reflux for 18h, return to room temperature and re...

Embodiment 2

[0041] Embodiment 2 (synthesis of p-toluenesulfonylimide)

[0042] Take a 250ml round bottom flask, add p-toluenesulfonamide (30mmol), sodium benzenesulfinate (30mmol), formic acid (45ml), H 2 O (45ml) and benzaldehyde (30mmol), stirred at room temperature for 3 days and filtered, the solid was washed with water, and then washed with petroleum ether, the solid was dissolved in a mixed solution of dichloromethane and sodium bicarbonate, stirred and filtered at room temperature, and the organic layer was used Wash with saturated brine, dry with anhydrous sodium sulfate, and remove the solvent by rotary evaporation to obtain the target compound (E)-N-benzylidene-4-methylbenzenesulfonamide, which can be further recrystallized. The yield is about 80%. Its reaction formula 6 is as follows:

[0043]

[0044] Reaction 6

Embodiment 3

[0046] Add 1mL of toluene to the reaction flask, then add 26mg (0.1mmol) of (E)-N-benzylidene-4-methylbenzenesulfonamide obtained in Example 2, and 48.8mg (0.2mmol) of Example 1 The obtained allenic acid ester (formula II) was stirred for 10 minutes, then 31.4 mg (0.12 mmol) of triphenylphosphine was added, stirred at room temperature for 12-15 h, monitored by TLC (petroleum ether: ethyl acetate = 3: 1), and obtained The lower point of p-toluenesulfonimide on the small plate is the product. After the reaction is completed, the product is separated by thin layer chromatography (petroleum ether: ethyl acetate=10:1), and the corresponding product (formula VI) is obtained. There are 36.6mg, and the yield is 77.7%. Its H NMR spectrum: 1 H NMR (600MHz, CDCl3) δ7.82 (d, J = 8.0 Hz, 1H), 7.75 (d, J = 8.2Hz, 1H), 7.35-7.27 (m, 7H), 5.25-5.05 (m, 2H) ,4.51(m,1H), 4.18-4.10(m,4H),3.08(m,1H),2.83(m,1H),2.66(m,1H),2.47(m,1H),2.46-2.43 (s ,3H), 2.25(m,1H), 1.29-1.23(m,6H).

[0047]

...

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Abstract

The invention discloses a method for synthesizing 2,3-dihydropyrrole rings from p-toluenesulfonyl imine and disubstituted allene under the condition of a phosphine catalyst. The method is a convenient route for synthesizing 2,3-dihydropyrrole ring compounds without a metal reagent, and an obtained hydrogenated pyrrole product is a common basic structure in certain bioactive molecules and has potential pharmacochemical study value. The method for synthesizing the 2,3-dihydropyrrole rings adopts mild conditions and simple and available raw materials, and 2-position different substituted 2,3-dihydropyrrole compounds can be prepared conveniently.

Description

technical field [0001] The invention relates to the field of pharmaceutical chemical synthesis, in particular to a method for synthesizing 2,3-dihydropyrrole ring and its derivatives by using sulfonimide and αγ disubstituted allenic acid ester. Background technique [0002] 2,3-Dihydropyrrole and its derivatives are the basic structural units of many pharmaceutical molecules and natural products with medicinal value, and are an important class of pharmaceutical intermediate structures. For example, spirotryprostatin B is a cell isolated from the marine fungus Aspergillus Cycle inhibitors, penem-like β-lactam antibiotics widely used in clinical practice, and myrmicarin 430A, the active ingredient of the venom gland secretion of the African brown ant, all contain structural fragments of 2,3-dihydropyrrole rings. [0003] [0004] Its derivatives are also widely used in polymer materials, new materials, food and other fields. Since the 2,3-dihydropyrrole ring structure is ub...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/48C07D405/04
CPCC07D207/48C07D405/04
Inventor 肖华孔祥文刘丽华
Owner HEFEI UNIV OF TECH
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