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A kind of method of synthesizing isoquinolinone compound

A technology for isoquinolinone and compound, which is applied in the field of synthesizing isoquinolinone and its derivatives, can solve the problems of harsh reaction conditions, low total yield, complicated operation, etc., and achieves good functional group tolerance and good application prospect. , overcome expensive effects

Inactive Publication Date: 2017-03-22
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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  • A kind of method of synthesizing isoquinolinone compound
  • A kind of method of synthesizing isoquinolinone compound
  • A kind of method of synthesizing isoquinolinone compound

Examples

Experimental program
Comparison scheme
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 and preparation methods used are:

[0032]

[0033] Binuclear copper salicylate 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 Add to the Scheck tube, the reaction solution is ventilated with oxygen 3 to 5 times under freezing of liquid nitrogen, and stirred at 30°C for 12 hours. After the reaction is over, 10mL of distilled water is added to the mixture, and then extracted three times with 15mL of dichloromethane. Collect the organic phase and use anhydrous Na 2 SO 4 Dry, filter with suction, remove the dichloromethane with a rotary evaporator, and separate by column chromatography to obtain 2-...

Embodiment 2

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

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 and preparation methods used are:

[0038]

[0039] In Example 1, the 2-phenyl-1,2,3,4-tetrahydroisoquinoline used was equimolar 2-p-methylphenyl-1,2,3,4-tetrahydroisoquine The other steps were the same as those in Example 1, and the white solid 2-p-tolyl-3,4-dihydroisoquinolin-1-one was obtained. The yield was 92%. The spectral data was: 1 H NMR(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=6.4 Hz, 2H), 3.13 (t, J=6.4 Hz, 2H), 2.37 (s, 3H); 13 C NMR(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 isoquinolinones and their derivatives, and specifically relates to the direct oxidation reaction of 2-aryl-1,2,3,4-tetrahydroisoquinoline compounds under the action of a copper catalyst and oxygen Method for the synthesis of isoquinolinone compounds. Background technique [0002] In synthetic chemistry and medicinal chemistry, exploring effective methods for the synthesis of isoquinolinones has become a very important research direction. As early as 1956, Hinton et al. used Dieckman condensation to synthesize isoquinolinone. In the following decades, the synthesis of isoquinolinone derivatives has been greatly developed. Traditional methods can be divided into the following categories: Dieckman condensation method, Bischler-Napieralski cyclization method, rearrangement method, Pd-catalysis method, etc. [0003] The synthesis method described in the literature is as follows: [0004] (1) Bischler-Na...

Claims

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Application Information

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