A kind of synthetic method of dihydropyrrolo 2-aminoquinoline compound

A technology of aminoquinoline and dihydropyrrole, which is applied in the field of synthesis of dihydropyrrolo-2-aminoquinoline compounds, can solve the problems of harsh reaction conditions, limitations, poor atom economy, etc., and achieve a convenient scope of application , mild conditions, and high atom economy

Active Publication Date: 2020-09-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the synthesis methods of such compounds, and generally multi-step synthesis is required, the atom economy is poor, and the conditions required for some reactions are harsh, which is limited in practical application (ACSChem.Neurosci.2016, 7, 972; Journal of Medicinal Chemistry, 1992, October, 1845)

Method used

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  • A kind of synthetic method of dihydropyrrolo 2-aminoquinoline compound
  • A kind of synthetic method of dihydropyrrolo 2-aminoquinoline compound
  • A kind of synthetic method of dihydropyrrolo 2-aminoquinoline compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add 0.2 mmol N-[4-(2-aminophenyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide, 0.02 mmol tetrakistriphenylphosphine palladium, 0.04 Millimol 1,3-di(diphenylphosphine) propane, 0.4 mmol anhydrous copper acetate and 2 ml of acetonitrile:toluene (1:1, v / v) mixed solvent, finally add 0.3 mmol isonitrile, in Stir and react at 100°C for 9 hours at 700 rpm; stop stirring, add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and dry with 0.5 g of anhydrous magnesium sulfate, filter, evaporate the solvent under reduced pressure, and pass through the column Chromatographic separation and purification, the column chromatography eluent used was a mixed solvent of petroleum ether: ethyl acetate with a volume ratio of 10:1 to obtain the target product with a yield of 65%.

[0039] The hydrogen spectrogram and carbon spectrogram of gained target product are respectively as follows figure 1 and figure 2 As shown, the structural characterization data are as ...

Embodiment 2

[0047] Add 0.2 mmol N-[4-(2-amino-5-methylphenyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide, 0.02 mmol tetratriphenyl phosphine palladium, 0.04 mmol 1,3-bis(diphenylphosphine) propane, 0.4 mmol anhydrous copper acetate and 2 ml of acetonitrile:toluene (1:1, v / v) mixed solvent, and finally add 0.3 ml mole of tert-butyl isonitrile, stirred and reacted at 100°C for 9 hours at 700 rpm; stopped stirring, added 5 mL of water, extracted 3 times with ethyl acetate, combined the organic phases and dried them with 0.5 g of anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure The solvent was removed, and then separated and purified by column chromatography. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 10:1 to obtain the target product with a yield of 54%.

[0048] The hydrogen spectrogram and carbon spectrogram of gained target product are respectively as follows image 3 and Figure 4 shown; th...

Embodiment 3

[0056] Add 0.2 mmol N-[4-(2-amino-3,5-dimethylphenyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide, 0.02 mmol Four triphenylphosphine palladium, 0.04 mmol 1,3-di(diphenylphosphine) propane, 0.4 mmol anhydrous copper acetate and 2 ml of acetonitrile:toluene (1:1, v / v) mixed solvent, finally Add 0.3 mmoles of tert-butylisonitrile, stir and react at 100°C at 700 rpm for 9 hours; stop stirring, add 5 mL of water, extract 3 times with ethyl acetate, combine organic phases and use 0.5 g of anhydrous magnesium sulfate to dry, filter, The solvent was distilled off under reduced pressure, and then separated and purified by column chromatography. The eluent used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 10:1 to obtain the target product with a yield of 58%.

[0057] The hydrogen spectrogram and carbon spectrogram of gained target product are respectively as follows Figure 5 and Figure 6 shown; the structural characterization dat...

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Abstract

The invention discloses a synthesis method of a dihydropyrrolo2-aminoquinoline compound. The synthesis method comprises the following steps: in a reactor, dissolving high-alkyne propylamine, a catalyst, an oxidant and a ligand into an organic solvent, and then adding isocyanide; stirring and reacting at 80 to 100 DEG C; after reaction is finished, cooling a reaction solution to room temperature; separating and purifying the reaction solution to obtain the dihydropyrrolo2-aminoquinoline compound. The synthesis method disclosed by the invention takes the simple and easy-to-obtain high-alkyne propylamine as a raw material, and isocyanide migration and inserting serial cyclization reaction is carried out; common palladium salt is used as the catalyst, and cheap copper salt is used as an oxidant to construct the dihydropyrrolo2-aminoquinoline compound with extremely good medicinal value; the synthesis method has the advantages of simple and easy-to-obtain raw materials, simplicity and safety in operation, moderate conditions and high atom economy; the synthesis method has the characteristics of high efficiency, convenience, wide applicable range and the like in the synthesis of a targetproduct and has potential value in actual production and application.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of dihydropyrrolo 2-aminoquinoline compounds. Background technique [0002] 2-Aminoquinoline and its derivatives are a very important class of compounds with a variety of biological and pharmaceutical activities, and are widely used in organic synthesis and pharmaceutical research. According to literature research, 2-aminoquinoline is currently mainly concentrated in Research and development of anti-depressant, anti-hypertensive, anti-cancer, anti-Alzheimer's disease and anti-protozoal drugs. At the same time, 2-aminoquinoline is also a commonly used synthon in organic synthesis, which can undergo cyclization reactions with alkyne bromides and isothiocyanates to efficiently synthesize a series of functional molecules (YGao, H.-F.Jing, Adv. Synth. Catal. 2013, 355, 2263; S. Manna, A.-P. Antonchick, Angew. Chem. Int. Ed. 2014, 53, 8163). G...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 伍婉卿李蒙江焕峰
Owner SOUTH CHINA UNIV OF TECH
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