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Synthesis of quinazoline-4 (3H) derivative

A synthesis method and derivative technology, applied in the direction of organic chemistry, etc., can solve the problems of low yield, long reaction time and high reaction temperature, and achieve the effects of high yield, simple method and mild reaction conditions.

Inactive Publication Date: 2004-10-20
EAST CHINA UNIV OF SCI & TECH
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Problems solved by technology

[0003] However, the main disadvantages of these synthetic methods are low yield (20-50%), long reaction time and high reaction temperature, especially these synthetic methods will pass through intermediate imine compounds, such as benzoxazine, Imines are easy to absorb moisture, unstable at high temperatures and difficult to purify. For this, in order to improve this reaction, chemists have done a lot of research work on this, such as using microwave promotion to carry out synthetic reactions (Kurosh Rad-Moghadam, MohammadS .Khajavi, J.Chem.Research (S), 1998, 702-703.), has also reached a certain effect, but the microwave promotion method is still in the research and exploration stage for organic synthesis

Method used

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  • Synthesis of quinazoline-4 (3H) derivative
  • Synthesis of quinazoline-4 (3H) derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Get anthranilic acid (10mmol, 1.37g), formic acid (13mmol, 0.78g) and aniline (13mmol, 1.41g) and catalyst Yb (OTf) 3 (0.5mmol, 62mg) were placed in a reaction flask and mixed together, heated and stirred, the temperature was controlled at 50°C, and the reaction was carried out for 60 minutes. The TLC was followed to complete the reaction. Then, water was added to quench the reaction, extracted three times with ethyl acetate, and the organic layers were combined. use Na 2 SO 4 Drying, rotary evaporation to remove the solvent, and recrystallization with ethanol to obtain the corresponding product, 1.64 g, yield 74%.

[0027] mp138-139°C, 1 H-NMR (500Hz, CDCl 3): δ8.32(d, 1H), 8.13(s, 1H), 7.60-7.72(m, J=27.29Hz, 2H), 7.44(t, J=14.34Hz, 1H), 7.23-7.31(m, J=38.12Hz, 5H); 13 C NMR (50MHz, CDCl 3 )δ160.5, 147.5, 146.4, 135.6, 134.3, 129.1, 128.3, 128.1, 127.1, 126.6, 127.2, 127.0, 122.1, 49.7; GC / MS: M + = 222.1; Anal. Calcd for C 14 h 10 N 2 OC, 75.66; H, 4.54; N,...

Embodiment 2

[0029] Get anthranilic acid (10mmol, 1.37g), trimethyl orthoformate (13mmol, 1.92g) and p-methylaniline (13mmol, 1.41g) and catalyst Yb (OTf) 3 (0.5mmol, 62mg) were mixed together in a reaction flask, heated and stirred, the temperature was controlled at 50°C, and the reaction was carried out for 10 minutes. The TLC was followed to complete the reaction. Then, water was added to quench the reaction, extracted three times with ethyl acetate, and the organic layers were combined. use Na 2 SO 4 Drying, rotary evaporation to remove the solvent, and recrystallization with ethanol to obtain the corresponding product, 2.31 g, yield 98%.

[0030] mp144-145°C, 1 H-NMR (500Hz, CDCl 3 ): δ8.22(d, 1H), 8.12(s, 1H), 7.61-7.71(m, J=24.23Hz, 2H), 7.42(t, J=13.31Hz, 1H), 7.15(d, J =8.6Hz, 2H), 6.88(d, J=8.5Hz, 2H), 2.33(s, 3H). 13 C NMR (50MHz, CDCl 3 )δ161.5, 144.5, 146.4, 135.3, 134.3, 129.0, 128.2, 128.1, 127.0, 126.5, 127.1, 127.0, 122.0, 49.6; GC / MS: M + =236; Anal. Calcd for C 1...

Embodiment 3

[0032] Catalyst Yb(OTf) 3 reuse of

[0033] Get anthranilic acid (10mmol, 1.37g), triethyl orthoformate (13mmol, 1.92g) and aniline (13mmol, 1.41g) and catalyst Yb (OTf) 3 (0.5mmol, 62mg) were mixed together in a reaction flask, heated and stirred, the temperature was controlled at 50°C, and the reaction was carried out for 10 minutes. The TLC was followed to complete the reaction. Then, water was added to quench the reaction, extracted three times with ethyl acetate, and the organic layers were combined. use Na 2 SO 4 Drying, rotary evaporation to remove the solvent, and recrystallization with ethanol to obtain the corresponding product, 2.17 g, yield 98%.

[0034] Catalyst Yb(OTf) 3 Stay in the water layer, remove the water by heating, then heat and vacuum at 100°C for 2-8 hours, and the catalyst is reused.

[0035] Under the same reaction conditions:

[0036] Catalyst Yb(OTf) 3 The first repetition yielded 2.15 g, a 97% yield.

[0037] Catalyst Yb(OTf) 3 The second...

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Abstract

The present invention discloses one method of synthesizing quinazoline-4(3H) derivative. An One-Step process in no-solvent condition is adopted, and in the process, o-aminobenzoic acid derivative, triethyl orthoformate, trimethyl orthoformate or formic acid and aromatic amine derivative are used as material, and trifluoromethnesulfonate of RE element is used as catalyst. Compared with available technology, the present invention has high yield up to 98%, short reaction period in 60 min, recoverable catalyst, and other advantages and is suitable for industrial production and environment friendly.

Description

technical field [0001] The invention relates to a synthesis method of 3H-quinazolin-4-one derivatives, in particular to a method for catalytically synthesizing 3H-quinazolin-4-one derivatives with a catalyst. Background technique [0002] 3H-quinazolin-4-one derivatives are widely used pharmaceutical intermediates with important pharmacological activities and can be used as anti-tumor, anti-cancer, diuretics, anticonvulsants, anti-enteritis agents, etc. Therefore, the research on its synthetic method is highly valued by chemists and medicinal chemists. The synthetic method of 3H-quinazolin 4-ketone derivative is also a lot, is generally to be starting raw material with the derivative of anthranilic acid, as: the reaction of anthranilic acid and imidate (David J.Connolly, Patrick J. Guiry, Synlett 2001, 11, 1707-1710), 2-fluorobenzoyl chloride and aminoheterocyclic imines (Martin J. Deetz, Jeremiah P. Malerich, Alicia M. Beatty, Bradley D. Smith, Terahedron Letters 42 , 185...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/88
Inventor 王利民田禾夏建俊秦芳
Owner EAST CHINA UNIV OF SCI & TECH
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