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Synthesis method for substituted 2, 3-dihydro-4(1H)-quinazolinone compound

A technology of quinazolinone and synthesis method, applied in the field of substitution 2, can solve the problems of expensive catalyst, use of toxic reagents, long reaction time and the like, and achieve the effects of short synthesis time, high product yield and low cost

Inactive Publication Date: 2015-02-18
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although certain effects have been obtained, some methods still have long reaction time, expensive catalyst and large dosage, and use of toxic reagents (CH 3 CN) and other shortcomings

Method used

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  • Synthesis method for substituted 2, 3-dihydro-4(1H)-quinazolinone compound
  • Synthesis method for substituted 2, 3-dihydro-4(1H)-quinazolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 110mmol isatoic anhydride, 100mmol benzaldehyde, 110mmol ammonium carbonate, 50mL ethanol / water mixed solution (volume ratio 1:3) to a 500mL reaction flask, heat and stir under reflux for 1h. After the reaction, the reaction bottle was cooled to room temperature, washed with ethanol / water (volume ratio 1:1), and filtered to obtain a crude product. The crude product was obtained by further recrystallization from absolute ethanol. The product is a white crystal with a yield of 90% and a melting point of 225-226°C.

[0018] IR(KBr): 3304, 3188, 1652, 1615, 1507, 1392, 1300, 1149, 748cm -1 ;

[0019] 1 H NMR (500MHz, DMSO-d 6 ): δ8.32(s, 1H), 7.62(d, J=7.2Hz, 1H), 7.50(d, J=6.8Hz, 2H), 7.42~7.35(m, 3H), 7.25(t, J= 8.4Hz, 1H), 7.14(s, 1H), 6.75(d, J=8.0Hz, 1H), 6.68(t, J=7.2Hz, 1H), 5.76(s, 1H);

[0020] Elemental Analysis C 14 h 12 N 2 O, found (calculated) (%): C 74.80 (74.98), H 5.51 (5.39), N 12.55 (12.49).

Embodiment 2

[0022] Add 110mmol isatoic anhydride, 100mmol 3-nitrobenzaldehyde, 110mmol ammonium carbonate, 50mL ethanol / water mixed solution (volume ratio 1:3) to a 500mL reaction flask, heat and stir under reflux for 2.7h. After the reaction, the reaction bottle was cooled to room temperature, washed with ethanol / water (volume ratio 1:1), and filtered to obtain a crude product. The crude product was obtained by further recrystallization from absolute ethanol. The product is a yellow crystal with a yield of 91% and a melting point of 200-202°C.

[0023] IR(KBr): 3337, 3147, 1673, 1635, 1526, 1386, 1187, 772cm -1 ;

[0024] 1H NMR (500MHz, DMSO-d 6 ): δ8.76(d, J=7.4Hz, 2H), 8.42(t, J=7.5Hz, 2H), 7.97(brs, 1H), 7.87(dt, J=6, 7.5Hz, 2H), 7.62 (brs, 1H), 7.57(t, J=6.2Hz, 1H), 7.38(t, J=7.5Hz, 1H), 7.26(s, 1H);

[0025] Elemental Analysis C 14 h 11 N 3 o 3 , found (calculated) (%): C 62.31 (62.45), H 4.07 (4.12), N 15.70 (15.61).

Embodiment 3

[0027] Add 110mmol isatoic anhydride, 100mmol 4-chlorobenzaldehyde, 110mmol ammonium acetate, 50mL ethanol / water mixed solution (volume ratio 1:3) to a 500mL reaction flask, heat and stir under reflux for 1h. After the reaction, the reaction bottle was cooled to room temperature, washed with ethanol / water (volume ratio 1:1), and filtered to obtain a crude product. The crude product was obtained by further recrystallization from absolute ethanol. The product is a white crystal with a yield of 90% and a melting point of 206-207°C.

[0028] IR (KBr): 3309, 3188, 1655, 1611, 1509, 1386, 1153, 753cm -1 ;

[0029] 1 H NMR (500MHz, DMSO-d 6 ): δ8.35(s, 1H), 7.62(d, J=8.8Hz, 2H), 7.49(dd, J=8.8, 8.8Hz, 3H), 7.26(t, J=7.6, 8.8Hz, 1H) , 7.15(s, 1H,), 6.75(d, J=8.0Hz, 1H), 6.69(t, J=7.2, 7.6Hz, 1H), 5.77(s, 1H);

[0030] Elemental Analysis C 14 h 11 N 2 OCl, found (calculated) (%): C 65.19 (65.00), H 4.23 (4.29), N 10.75 (10.83).

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Abstract

The invention discloses a synthesis method for a substituted 2, 3-dihydro-4(1H)-quinazolinone compound, and belongs to the field of medicinal preparations. According to the method, the three-component one-pot reaction of isatoic anhydride, aromatic aldehyde and ammonium salt / aromatic amine can be efficiently implemented in an ethanol / water mixed solvent without a catalyst under a reflux condition. The method has the characteristics of low cost, environment friendliness, short synthesis time and high product yield.

Description

technical field [0001] The invention relates to the field of pharmaceutical preparations, in particular to a method for synthesizing substituted 2,3-dihydro-4(1H)-quinazolone compounds. Background technique [0002] 2,3-Dihydroquinazolinones are a class of nitrogen-containing heterocyclic compounds with good biological and pharmacological activities. It shows excellent activity in sterilization, diuresis, anti-cancer, etc., and is a hot spot of research by pharmacologists. [0003] The typical synthesis methods of this type of compound mainly include: (a) taking anthranilamide and aldehyde or ketone as raw materials, and p-toluenesulfonic acid as a catalyst in an organic solvent; (b) in SmI 2 or TiCl 4 -Under Zn catalysis, o-nitrobenzamide reacts with aldehyde or ketone in anhydrous and oxygen-free environment; (c) with isatoic anhydride and Schiff base as raw materials, react under acid or alkaline conditions; ( d) desulfurization reaction of 2-thio-4(3H)-quinazolinone; ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91
CPCC07D239/91
Inventor 宋志国曹春艳赵永华
Owner BOHAI UNIV
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