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A kind of method for synthesizing 4-hydro-pyrrole[3,2-c]pyridin-4-one compounds

A ketone compound, 2-c technology, applied in the field of synthesizing 4hydro-pyrrole[3,2-c]pyridin-4-one compounds, can solve the problem of unfavorable large-scale industrial production, cumbersome operation and increased reaction cost and other problems, to achieve the effect of easy operation, simple reaction process and few experimental steps

Inactive Publication Date: 2020-04-28
HENAN NORMAL UNIV
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Problems solved by technology

Some of these methods use a combination of multiple noble metal catalysts, strong acid catalysis or multi-step reaction strategies, which not only makes the operation cumbersome, but also increases the reaction cost, which is not conducive to large-scale industrial production.

Method used

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  • A kind of method for synthesizing 4-hydro-pyrrole[3,2-c]pyridin-4-one compounds
  • A kind of method for synthesizing 4-hydro-pyrrole[3,2-c]pyridin-4-one compounds
  • A kind of method for synthesizing 4-hydro-pyrrole[3,2-c]pyridin-4-one compounds

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example 1

[0021] Add N-(4-chlorobenzene)-2-methyl-1-(p-tolyl)-4,5-dihydro-1 hydrogen-pyrrole-3-carboxamide (130 mg, 0.4 mmol), benzaldehyde (46 mg, 0.44 mmol), ammonium acetate (308.3 mg, 4 mmol) and solvent PEG-400 (2 ml), the reaction mixture was heated on an oil bath, and the reaction process was performed using LC-MS After the reaction is completed, the system is naturally cooled to room temperature, and after extraction, liquid separation, drying, and column chromatography operation, 5-(4-chlorophenyl)-6-phenyl-1-(p-tolyl)-1 can be obtained , 2,3,5,6,7-Hexahydro-4hydro-pyrro[3,2-c]pyridin-4-one (119 mg, 72%).

[0022]

[0023] 5-(4-chlorophenyl)-6-phenyl-1-(p-tolyl)-1,2,3,5,6,7-hexahydro-4hydro-pyrrole[3,2-c]pyridine -4-one

[0024]White solid, yield: 72%, melting point: 181-182°C; 1 H NMR (400MHz, CDCl 3 )δ7.27-7.16(m, 5H), 7.13(d, J=8.8Hz, 2H), 7.06(m, 4H), 6.73(d, J=8.0Hz, 2H), 5.11-5.04(m, 1H ), 3.96-3.88(m, 2H), 3.36-3.30(dd, J=16.8, 5.6Hz, 1H), 3.08-3.00(m, 1H), 2.95-...

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Abstract

A method for synthesizing 4-hydro-pyrrole[3,2-c]pyridine-4-one compounds. Using 2-arylamino-N-arylpyrrole compounds and aldehyde compounds as raw materials, ammonium acetate as a catalyst, and PEG-400 as a solvent, 4 hydrogen-pyrrole[3,2-c is prepared in the next step under heating conditions ] Pyridin-4-one compounds. After the reaction is completed, the 4-hydro-pyrrole[3,2-c]pyridine-4-one compound can be obtained through operations such as cooling, suction filtration and separation. The reaction step is only one step, the process is simple, and the raw materials, catalysts and solvents are cheap and easily available chemical raw materials; the reaction has the advantages of high efficiency, simple operation, good functional group compatibility, good regioselectivity, and high product yield. bright future.

Description

technical field [0001] The invention relates to a method for synthesizing 4hydro-pyrrole[3,2-c]pyridin-4-one compounds, specifically using ammonium acetate as a catalyst and PEG-400 as a solvent to make 2 -A method for generating 4-hydro-pyrrole[3,2-c]pyridin-4-one compounds through an intermolecular series reaction between an arylamino-N-arylpyrrole compound and an aldehyde compound. The method has the advantages of wide applicability, simple operation, good functional group compatibility, good regioselectivity and high product yield. Background technique [0002] 4H-pyrrole[3,2-c]pyridin-4-ones have various biological activities. Further cyclization via functionalized pyrroles is a common method for the preparation of such compounds. Literature Beccalli, E.M.; Broggini, G.; Martinelli, M.; Paladino, G.Tetrahedron 2005, 61, 1077-1082, using o-formylpyrrole as raw material, prepared 4 hydrogen-pyrrole[3,2- c] pyridin-4-ones, but at the same time, another regioselective is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 张志国黄媛媛麻娜娜张贵生刘青锋
Owner HENAN NORMAL UNIV
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