Preparation method of polysubstituted pyrrole compound

A compound and multi-substitution technology, which is applied in the field of preparation of multi-substituted pyrrole compounds, can solve the problems of severe conditions and poor chemical selectivity, and achieve the effects of high reactivity, wide application range and high yield

Inactive Publication Date: 2018-08-03
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthesis of pyrrole by condensation usually faces problems such as poor chemical selectivity and severe conditions. [3]

Method used

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  • Preparation method of polysubstituted pyrrole compound
  • Preparation method of polysubstituted pyrrole compound
  • Preparation method of polysubstituted pyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of 2-{[(4-phenyl-1-en-3-yne)-2-butyl]}-1-p-toluenesulfonylpyrrole

[0054]

[0055] Add proline methyl ester hydrochloride (5g, 30.3mmol) in the round bottom flask of 250mL, p-toluenesulfonyl chloride (5.76g, 30.3mmol), then add 200mL methylene chloride as solvent in the flask, then Triethylamine (6.13 g, 60.6 mmol) was added dropwise thereto. After the dropwise addition, the reaction was stirred at room temperature for 20 h. After the reaction was complete, 200 mL of water was added to quench the reaction. Extract with dichloromethane, combine organic phase, after using 1M dilute hydrochloric acid washing, organic phase is dried with anhydrous magnesium sulfate, and rotary evaporation removes organic solvent, obtains the N-p-toluenesulfonylproline methyl ester of target (8.15g , yield 95%).

[0056] The N-p-toluenesulfonyl proline methyl ester (5g, 17.6mmol) obtained in the previous step was dissolved in anhydrous tetrahydrofuran (100mL), and N, O-dime...

Embodiment 2

[0060] Preparation of N,4-methyl-N-[(3-methylene-1,5-diphenyl-4-yne)-2-pentyl]benzenesulfonamide

[0061]

[0062] Add phenylalanine methyl ester hydrochloride (5g, 23.2mmol) in the round bottom flask of 250mL, p-toluenesulfonyl chloride (4.4g, 23.2mmol), then add 200mL methylene chloride as solvent in the flask, Then triethylamine (4.67 g, 46.4 mmol) was added dropwise thereto. After the dropwise addition, the reaction was stirred at room temperature for 20 h. After the reaction was complete, 200 mL of water was added to quench the reaction. Extract with dichloromethane, combine organic phase, after using 1M dilute hydrochloric acid washing, organic phase is dried with anhydrous magnesium sulfate, and remove organic solvent with rotary evaporation, obtain the N-p-toluenesulfonyl phenylalanine methyl ester of target (7.4 g, yield 96%).

[0063] In the round bottom flask of 50mL, add N-p-toluenesulfonyl phenylalanine methyl ester (3.1g, 9.3mmol), anhydrous potassium carbon...

Embodiment 3

[0068] Preparation of 7-methyl-5-phenyl-6-p-toluenesulfonyl-2,3-dihydro-1H-pyrine

[0069]

[0070] Under nitrogen protection, a magnetic stirrer was added to a clean round bottom flask, 1mL of 1,2-dichloroethane was added, and IPrAuCl (0.005mmol, 3.1mg), AgNTf 2 (0.005mmol, 1.9mg), stirred for 10min, then added 2-{[(4-phenyl-1-ene-3-yne)-2-butyl]}-1-p-toluenesulfonylpyrrole (0.1mmol, 35mg), reacted at 40°C for 8h. After the reaction, the reaction solution was filtered through short silica gel, the filtrate was concentrated, and separated by column chromatography to obtain the target product. The developer ratio is petroleum ether:ethyl acetate=5:1, and the final product is a white solid with a yield of 74%.

[0071] Its physical constant of the product that present embodiment makes is: 1 HNMR (CDCl 3,400MHz) 1 H NMR (400MHz, CDCl 3 )δ7.53(d, J=8.1Hz, 2H), 7.46–7.29(m, 5H), 7.15(d, J=8.0Hz, 2H), 3.71(t, J=7.1Hz, 2H), 2.79( t,J=7.2Hz,2H),2.42(q,J=7.2Hz,2H),2.36(s,3H),...

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Abstract

The invention discloses a preparation method of a polysubstituted pyrrole compound. The preparation method comprises steps as follows: an alkyne enamine compound is subjected to a cyclization reactionunder the catalytic action of univalent gold, a product is subjected to column chromatography or recrystallization separation, and a fully substituted pyrrole compound is obtained; substituent groupscan be removed from the pyrrole compound under the proper condition, and a tetra-substituted pyrrole compound is obtained. The chain-like alkyne enamine compound is subjected to the cyclization reaction, and the fully substituted or tetra-substituted pyrrole compound is obtained. The preparation method has the advantages that the operation is simple, steps are simple, the reaction is efficient, raw materials are cheap and easy to obtain, the pilot plant test can be amplified and the like.

Description

technical field [0001] The invention relates to the field of synthesis of pyrrole compounds, in particular to a preparation method of multi-substituted pyrrole compounds. Background technique [0002] Pyrrole and its derivatives are widely used in the organic synthesis industry, and are important raw materials or key intermediates of fine chemicals such as pharmaceuticals, pesticides, and spices. Compounds containing pyrrole structural units widely exist in nature. Due to their special structure, they show important biological activities. Many natural products or drug molecules contain pyrrole units. [1] . (Document 1: (a) Paris, D.; Cottin, M.; Demonchaux, P.; Augert, G.; Dupassieux, P.; Lenoir, P.; Peck, M.J.; Jasserand, D.J.Med.Chem.1995, 38,669; (b) Fernandez, L.S.; Buchanan, M.S.; Caroll, A.R.; , T.; Yasue, K.; Matsumoto, K.; Kajimoto, Y.; Ogo, T.; Inaba, T. Org. Lett. 2007, 9, 3331; (d) Wilson, R.M.; , R.G.; Ellman, J.A.Org.Lett.2006, 8, 1745; (e) Schrader, T.O.; J...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D207/36C07D471/04
CPCC07D207/36C07D471/04C07D487/04
Inventor 祝诗发吴烽王永东黄志鹏陈莲芬
Owner SOUTH CHINA UNIV OF TECH
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