Preparation method for 2,4-disubstituted-1,3,5-triazine derivatives

A technology of triazine derivatives and disubstitution, applied in the direction of organic chemistry, can solve the problems of low yield and harsh reaction conditions, and achieve the effect of simple reaction system, easy synthesis and mild conditions

Active Publication Date: 2017-06-20
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of method usually has the disadvantages of harsh reaction conditions and low yield. This paper

Method used

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  • Preparation method for 2,4-disubstituted-1,3,5-triazine derivatives
  • Preparation method for 2,4-disubstituted-1,3,5-triazine derivatives
  • Preparation method for 2,4-disubstituted-1,3,5-triazine derivatives

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Embodiment 1

[0015] In order to better understand the present invention, the synthesis of symmetric 2,4-disubstituted-1,3,5 triazine derivatives is illustrated by the following examples.

[0016]

[0017] In the reaction tube, add AgSbF in an argon atmosphere 6 (0.015mmol), amidine (1) (Ar 1 Is phenyl 0.4mmol) and benzyl isonitrile (2) (0.3mmol), then add the solvent toluene (3mL), stir under heating at 140℃ for about 10 hours, stop the reaction, cool to room temperature, transfer the reaction solution into the In the steaming flask, the solvent was removed by distillation under reduced pressure, the residue was dissolved in dichloromethane and loaded, using 300-400 mesh silica gel as the stationary phase, and the mixed solution of petroleum ether: ethyl acetate = 50:1 (volume ratio) The eluent is subjected to silica gel column chromatography, nuclear magnetic and liquid mass spectrometry detection, and 2,4-disubstituted-1,3,5 triazine (Ar 1 Is phenyl) consistent.

[0018] The following table s...

Embodiment 9

[0022] In order to better understand the present invention, the following examples illustrate the synthesis of asymmetric 2,4-disubstituted-1,3,5 triazine derivatives.

[0023]

[0024] In the reaction tube, add AgSbF in an argon atmosphere 6 (0.015mmol), amidine (1) (Ar 1 Is 4-chlorophenyl 0.2mmol), amidine (1’) (Ar 2 Is 4-bromophenyl 0.2mmol) and benzyl isonitrile (2) (0.3mmol), then add the solvent toluene (3mL), stir under heating at 140℃ for about 10 hours, stop the reaction, cool to room temperature, and remove the reaction solution Transfer to a rotary steaming flask, remove the solvent by distillation under reduced pressure, dissolve the residue in dichloromethane and load the sample, use 300-400 mesh silica gel as the stationary phase, and use petroleum ether: ethyl acetate = 50:1 (volume ratio) The mixed solution is used as the eluent for silica gel column chromatography, nuclear magnetic and liquid mass spectrometry detection, and 2,4-disubstituted-1,3,5 triazine (Ar 1 ...

Embodiment 2

[0033]

[0034] 2,4-Bis(4-methoxyphenyl)-1,3,5-triazine(3b)

[0035] Yield: 46.3mg (82%), white solid. 1 H NMR(400MHz, CDCl 3 )δ9.07(s,1H), 8.54(d,J=7.4Hz,4H), 6.99(d,J=7.4Hz,4H), 3.86(s,6H); 13 C NMR(100MHz, CDCl 3 )δ170.6, 166.4, 166.1, 163.5, 131.0, 130.8, 128.3, 114.3, 114.1, 55.5.

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Abstract

The invention relates to a preparation method for symmetric and asymmetric 2,4-disubstituted-1,3,5-triazine derivatives. Specifically, substituted amidine reacts with benzyl isocyanide under the catalysis of a silver salt or copper salt so as to produce the symmetric and asymmetric 2,4-disubstituted-1,3,5-triazine derivatives. The method is simple in reaction system, mild in reaction condition and wide in substrate range.

Description

Technical field [0001] The invention relates to a method for preparing symmetric and asymmetric 2,4-disubstituted-1,3,5 triazine derivatives. Specifically, it is the reaction of substituted amidines and benzyl isonitriles catalyzed by silver or copper salts to generate symmetric and asymmetric 2,4-disubstituted-1,3,5 triazine derivatives. Background technique [0002] Triazines are an important class of nitrogen-containing heterocyclic compounds with a wide range of biological activities and medical value (Document 1: (a) Saleh, M.; Abbott, S.; Perron, V.; Lauzon, C.; Penney, C.; Zacharie, B. Bioorg. Med. Chem. Lett., 2010, 20, 945. (b) Melato, S.; Prosperi, D.; Coghi, P.; Basilico, B.; Monti, D. ChemMedChem, 2008 ,3,873.(c)Zhu,W.; Liu,Y.; Zhao,Y.; Wang,H.; Tan,L.; Fan,W.; Gong,P.Arch.Pharm.Chem.Life Sci., 2012, 345, 812. (d) Patel, RV; Kumari, P.; Rajani, DP; Chikhalia, KHEur. J. Med. Chem., 2011, 46, 4354.). In the preparation of liquid crystal materials (Document 2: (a) (a)...

Claims

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Application Information

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IPC IPC(8): C07D251/24C07D409/14C07D409/04
CPCC07D251/24C07D409/04C07D409/14
Inventor 万伯顺鹿晓东信晓义吴凡
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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