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Method for synthesizing isoquinoline ketone compounds

A technology for isoquinolinones and compounds, which is applied in the field of synthesizing isoquinolinones and their derivatives, can solve the problems of complex operation, low total yield, harsh reaction conditions, etc. Effects of functional group tolerance

Inactive Publication Date: 2015-12-16
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions of this synthetic method are relatively harsh, the operation is complicated, and the total yield is not high.

Method used

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  • Method for synthesizing isoquinoline ketone compounds
  • Method for synthesizing isoquinoline ketone compounds
  • Method for synthesizing isoquinoline ketone compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Taking the preparation of 2-phenyl-3,4-dihydroisoquinolin-1-one with the following structural formula as an example, the raw materials used and the preparation method are:

[0032]

[0033] Dinuclear salicylic acid copper complex 1.9mg (0.0025mmol), TBAC (tetrabutylammonium chloride) 1.4mg (0.005mmol), 2-phenyl-1,2,3,4-tetrahydroisoquinoline 52mg (0.25mmol), 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazoline chloride (provided by Shanghai Aladdin Biochemical Technology Co., Ltd.) 13.4mg (0.01mmol), 1.0mL acetonitrile Put it into the Scheck tube, and the reaction solution was ventilated with oxygen for 3 to 5 times under liquid nitrogen freezing, and stirred at 30°C for 12 hours. After the reaction was completed, 10 mL of distilled water was added to the mixture, and then extracted three times with 15 mL of dichloromethane. The organic phase was collected and washed with anhydrous Na 2 SO 4 Drying, suction filtration, removal of dichloromethane with a rotary evaporator,...

Embodiment 2

[0035] In embodiment 1, the 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazoline chloride used is replaced with equimolar thiamine hydrochloride (vitamin B1), other steps are the same as in embodiment 1 Likewise, 2-phenyl-3,4-dihydroisoquinolin-1-one was obtained in 90% yield.

Embodiment 3

[0037] Taking the preparation of 2-p-tolyl-3,4-dihydroisoquinolin-1-one with the following structural formula as an example, the raw materials used and the preparation method are:

[0038]

[0039] In Example 1, 2-phenyl-1,2,3,4-tetrahydroisoquinoline was used with equimolar 2-p-methylphenyl-1,2,3,4-tetrahydroisoquinoline Phenyl is replaced, and other steps are identical with embodiment 1, obtains white solid 2-p-tolyl-3,4-dihydroisoquinolin-1-one, and its productive rate is 92%, and spectral data is: 1 HNMR (400MHz, CDCl 3 )δ: 8.16(d, J=7.6Hz, 1H), 7.47(td, J=1.6Hz, J=7.2Hz, 1H), 7.37(t, J=7.2Hz, 1H), 7.28-7.21(m, 5H), 3.97(t, J=6.4Hz, 2H), 3.13(t, J=6.4Hz, 2H), 2.37(s, 3H); 13 CNMR (100MHz, CDCl 3 )δ: 164.2, 140.5, 138.2, 136.0, 131.9, 129.8, 129.5, 128.7, 127.1, 126.9, 49.5, 28.6, 21.0; IR (KBr), ν (cm -1 ): 3411, 3127, 1658, 1402, 1320, 826, 741, 619; HRMS (ESI) m / z: C 16 h 15 NNaO[M+Na] + The theoretical value is 260.1051, and the measured value is 260.1045.

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Abstract

The invention discloses a method for synthesizing isoquinoline ketone compounds. The method includes that dual-core salicylic acid copper complexes which are cheap and easy to synthesize are taken as catalyzers, oxygen which is green, environment-friendly and nontoxic is taken as an oxidizing agent, chlorine salt, 3-benzyl-5-(2-hydroxy ethyl) -4-methyl thiazole moiety or thiamine hydrochloride are taken as auxiliary catalizers, and 2-aryl-1,2,3,4-tetrahydroisoquinoline compounds are subjected to further reaction to obtain the isoquinoline ketone compounds. The method is simple in operation, the catalyzers are cheap and easy to obtain, reaction conditions are moderate, product yield is high, shortcomings that traditional raw material reagents are high in price, harsh in condition, complex in synthesizing step, low in overall yield and the like are overcome, and good application prospect is achieved.

Description

technical field [0001] The invention belongs to the technical field of synthesizing isoquinolones and derivatives thereof, and specifically relates to the direct oxidation reaction of 2-aryl-1,2,3,4-tetrahydroisoquinoline compounds under the action of copper catalyst and oxygen A method for synthesizing isoquinolinones. Background technique [0002] In synthetic chemistry and medicinal chemistry, exploring effective methods for synthesizing isoquinolinones has become a very important research direction. As early as 1956, Hinton et al. used Dieckman condensation to realize the synthesis of isoquinolinones. In the following decades, the synthesis methods of isoquinolinone derivatives have been greatly developed. Traditional methods can be mainly divided into the following categories: Dieckman condensation method, Bischler-Napieralski cyclization method, rearrangement method, Pd-catalysis method and so on. [0003] The synthesis method described in the literature is as follow...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24
CPCC07D217/24
Inventor 王超刘玉霞薛东肖建良
Owner SHAANXI NORMAL UNIV
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