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Method for synthesizing quinazoline-4-(3H)-ketone

A technology for synthesizing quinazoline and crystallization, which is applied in the field of drug synthesis, can solve the problems of complex post-processing, poor stability, and long reaction time, and achieve the effects of wide application range, mild reaction conditions, and short reaction time

Inactive Publication Date: 2012-07-18
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In summary, in the known synthetic methods of quinazolin-4(3H)-ones, either the temperature is higher, or the reaction time is longer, or the required reagents are expensive, difficult to preserve, poor in stability, and complicated to use , post-processing complex
These deficiencies have brought a lot of inconvenience to the synthesis of this type of compound, especially industrialized production

Method used

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  • Method for synthesizing quinazoline-4-(3H)-ketone
  • Method for synthesizing quinazoline-4-(3H)-ketone
  • Method for synthesizing quinazoline-4-(3H)-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 20mL of dried toluene to a 100ml single-necked bottle, add 10mmol of 2-aminobenzonitrile under stirring, then add 15mmol of p-chlorobenzaldehyde, 2mmol of sodium hydroxide, and heat to reflux for 2h. After the reaction was completed, the reaction solution was poured into 20 mL of aqueous solution, extracted with ethyl acetate, and dried by rotary evaporation. Then crystallize with ethanol to obtain the product 2-(4-chlorophenyl)quinazolin-4(3H)-one. Yield 83%, Mp.>300°C.

[0029]

[0030] 1 H NMR (DMSO-d 6 , 400MHz) δ: 7.54-7.61 (m, 2H, ArH), 7.67 (d, J=7.6Hz, 1H, ArH), 7.77 (d, J=8.0Hz, 1H, ArH), 7.84-7.88 (m, 1H, ArH), 8.14-8.18(m, 2H, ArH), 8.24(s, 1H, ArH), 12.64(s, 1H, NH). MS(ESI): m / z(%)=257.0(100) [M+H] +

Embodiment 2

[0032] Use acetaldehyde instead of p-chlorobenzaldehyde, and the others are the same as in Example 1 to obtain the target product 2-methylquinazolin-4(3H)-one. Yield 75%. Mp.238-240°C.

[0033]

[0034] 1 H NMR (DMSO-d 6 , 300MHz) δ: 12.19 (s, br, 1H), 8.07 (d, 1H, J=8.1Hz), 7.77 (t, 1H, J=7.5Hz), 7.56 (d, 1H, J=7.9Hz), 7.45(t, 1H, J=7.5Hz), 2.36(s, 3H); 13 C NMR (DMSO-d 6 , 75MHz) δ: 162.2, 154.8, 149.5, 134.8, 127.1, 126.4, 126.2, 121.2, 21.9. MS (ESI) m / z (%) = 161.2 (100) [M+H] +

Embodiment 3

[0036] Replace 2-aminobenzonitrile with 5-nitro-2-aminobenzonitrile, replace p-chlorobenzaldehyde with p-methoxybenzaldehyde, and others are the same as in Example 1 to obtain target product 2-(4-methoxybenzene base)-6-nitroquinazolin-4(3H)-one, the yield was 71%. Mp.>300°C.

[0037]

[0038] 1 H NMR (DMSO-d 6 )δ: 12.83(s, 1H, NH), 8.80(d, 1H, J=2.4Hz, ArH), 8.53(dd, 1H, J=2.4, 8.0Hz, ArH), 8.25(d, 2H, J= 8.0Hz, ArH), 7.86(d, 1H, J=8.0Hz, ArH), 7.12(d, 2H, J=8.0Hz, ArH), 3.85(s, 1H, CH 3 ); 13 C NMR (DMSO-d 6)δ: 55.6, 114.2, 114.2, 114.2, 120.6, 122.1, 124.0, 128.5, 130.2, 130.2, 130.2, 144.3, 155.2, 161.7, 162.7; MS (ESI): m / z (%) = 298.1 (100) [ M+H] +

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Abstract

The invention provides a method for synthesizing quinazoline-4-(3H)-ketone and belongs to the field of organic synthesis. A reaction formula is expressed in a figure, wherein a reacting alkali is diethylamine, triethylamine, ammonium acetate, sodium (potassium) hydroxide and sodium (potassium) alkoxide; a reacting solvent is 1,4-dioxane, n-hexane, cyclohexane, tetrahydrofuran, benzene, toluene and dimethylbenzene; and the reaction implementation is conventional heating. According to the method, 2-amino-nitrile compound is taken as a raw material and is blended with aldehyde under the action of alkali, thereby synthesizing the quinazoline-4-(3H)-ketone in one step. The method has the advantages that the raw material is easily obtained, the process is simple, the reaction condition is mild, the reaction application scope is wide, the post-processing is simple and different substrates can be used for synthesizing the quinazoline-4-(3H)-ketone.

Description

(1) Technical field [0001] The invention relates to a method for preparing quinazoline-4(3H)-ones (English name quinazoline-4(3H)-ones) through the reaction of o-aminoaromatic nitriles and aldehydes, belonging to the field of drug synthesis. (2) Background technology [0002] Quinazoline 4(3H) ketone heterocyclic compounds have good biological activity and pharmaceutical activity, and are an important class of natural products, pharmaceutical and fine chemical intermediates, and can be used in the synthesis of various drugs. For example, compound A [2-methyl-quinazolin-4(3H)-one] is a natural product extracted from Bacillus cereus (Antibiot, 1991, 44, 111), compound B [2-(4-hydroxybutyl )quinazolin-4(3H)-one] from Dichroafebrifuga (Chin. Pharm. Sci. 2000, 9, 116). Compound C[3-(2-chlorophenyl)-6-fluoroquinazolin-4(3H)-one] is a potential AMPA antagonist (Bioorg.Med.Chem.Lett.2000, 10,1203; J.Med.Chem.2001,44,1710); Compound D[2-methyl-3-o-benzylquinazolin-4(3H)-one] (J.Med...

Claims

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Application Information

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IPC IPC(8): C07D239/91C07D239/90C07D405/04C07D401/04
Inventor 李加荣唐健红刘长娥史大昕张奇
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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