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Preparation method of 3,4-cycloalkylquinoline-2(1H)-one compound

A technology of ketone compounds and cycloalkylquinolines, which is applied in the field of preparation of 3,4-cycloalkylquinolin-2(1H)-one compounds, and can solve problems such as no specific records

Active Publication Date: 2019-11-29
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although previous work has described the synthesis methods of different 3,4-cycloalkylquinolin-2(1H)-ones, there is no specific description of the 3,4-cycloalkanes mentioned in this patent. The synthetic method of quinolin-2 (1H)-ketone compound

Method used

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  • Preparation method of 3,4-cycloalkylquinoline-2(1H)-one compound
  • Preparation method of 3,4-cycloalkylquinoline-2(1H)-one compound

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Experimental program
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Effect test

Embodiment 1

[0017]

[0018] At room temperature, N-methoxycyclohexene-1-carboxamide (10mmol), phenyl pinacol ester (20mmol), silver oxide (40mmol), rhodium catalyst (4mol%) were added successively in a pressure-resistant reaction tube and methanol (10 mL). The reaction mixture was then reacted at 80°C for 20 hours. Stop the reaction, concentrate under reduced pressure to obtain the crude product, and finally wash with a mixed eluent of petroleum ether and ethyl acetate, and perform flash column chromatography to obtain the target product 3a. Yield 89%. yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ=7.71(d, J=8Hz, 1H), 7.58-7.63(m, 1H), 7.54(t, J=7.6Hz, 1H), 7.23-7,29(m, 1H), 4.08(s, 3H), 2.85 (s, 2H), 2.69 (s, 2H), 1.76-1.91 (m, 4H).

Embodiment 2

[0020]

[0021] At room temperature, add N-methoxycyclohexene-1-carboxamide (10mmol), p-methoxyphenyl pinacol ester (30mmol), silver oxide (30mmol), rhodium catalyst successively in the pressure-resistant reaction tube (4mol%) and methanol (10mL). The reaction mixture was then reacted at 70°C for 24 hours. Stop the reaction, concentrate under reduced pressure to obtain the crude product, and finally wash with a mixed eluent of petroleum ether and ethyl acetate, and perform flash column chromatography to obtain the target product 3c. Yield 84%. Yellow solid, m.p.109.7-111.2°C; 1 HNMR (400MHz, CDCl 3 )δ=7.60(d, J=7.2Hz, 1H), 7.06(d, J=2.4Hz, 1H), 6.84(dd, J=2.4Hz, J=2.8Hz, 1H), 4.08(s, 3H) , 3.92 (s, 3H), 2.77-2.85 (m, 2H), 2.60-2.70 (m, 2H), 1.75-1.90 (m, 4H).

Embodiment 3

[0023]

[0024] At room temperature, N-methoxycyclohexene-1-carboxamide (10mmol), p-fluorophenyl pinacol ester (35mmol), silver oxide (40mmol), rhodium catalyst (4mol) were added successively in the pressure-resistant reaction tube. %) and ethanol (10 mL). The reaction mixture was then reacted at 100°C for 24 hours. Stop the reaction, concentrate under reduced pressure to obtain the crude product, and finally wash with a mixed eluent of petroleum ether and ethyl acetate, and perform flash column chromatography to obtain the target product 3c. Yield 80%. yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ=7.64-7.72(m, 1H), 7.24-7.32(m, 1H), 6.93-7.02(m, 1H), 4.08(s, 3H), 2.82(s, 2H), 2.67(s, 2H) , 1.76-1.90 (m, 4H).

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Abstract

The invention relates to a preparation method of a 3,4-cycloalkylquinoline-2(1H)-one compound. The preparation method comprises the following steps: dissolving raw material N-methoxy-1-cycloalkenamideand different aryl boronicacidpinacolesters in methanol; then adding silver oxide and a rhodium catalyst; carrying out reacting for 6-24 hours at a temperature of 20-100 DEG C; and separating and purifying a crude product after the reaction is ended to obtain the 3,4-cycloalkylquinoline-2(1H)-one compound. The preparation method has the advantages that the raw materials are simple and are easilyavailable, operation is simple, the yield is high, the application range of a substrate is wide, and the prepared product is easy to purify.

Description

[0001] (1) Technical field [0002] The invention belongs to the field of organic synthetic chemistry and relates to a preparation method of 3,4-cycloalkylquinolin-2(1H)-ketone compounds, in particular to a method of silver oxide and dichloro(pentamethylcyclopentadiene) Alkenyl) rhodium (III) dimer catalyst (hereinafter referred to as: rhodium catalyst) mediated direct utilization of N-methoxy-1-cycloalkenenamide and different arylboronic acid pinacol esters via hydrocarbon activation reaction A method for coupling and synthesizing 3,4-cycloalkylquinolin-2(1H)-one compounds. [0003] (2) Background technology [0004] 3,4-Cycloalkylquinolin-2(1H)-one compounds are an important class of organic structural units, which widely exist in various natural products, drug molecules and pharmaceutical intermediates with biological activity, making 3, The research on 4-cycloalkylquinolin-2(1H)-one derivatives, especially the preparation method of this kind of compounds, has been develope...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07D221/16C07D491/052C07D471/04
CPCC07D221/12C07D221/16C07D491/052C07D471/04
Inventor 朱有全回立稳牛云霞孔祥蕾朱堃
Owner NANKAI UNIV
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