Method for synthesizing 1H,3H-quinazoline-2,4-diketone

A quinazoline and diketone technology, applied in the field of 1H synthesis, can solve the problems of expensive reagents, complicated operation, and high toxicity, and achieve the effects of increased yield, reduced pollution, and reduced damage

Inactive Publication Date: 2010-05-12
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to solve the problems of traditional synthesis of 1H, 3H-quinazoline-2,4-dione with complex operation, low yield, expensive reagents, high toxicity, etc., and propose a method using o-aminoaromatic nitrile Reacting with N-alkyl formamide to synthesize 1H, the method of 3H-quinazoline-2,4-dione

Method used

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  • Method for synthesizing 1H,3H-quinazoline-2,4-diketone

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Embodiment 1

[0025] 2-Aminobenzonitrile (0.3g, 0.002mol), DMF (8.0mL), anhydrous zinc chloride (0.27g, 0.002mol), the mixture was added to the autoclave, 0.1ml of concentrated hydrochloric acid was added dropwise, oil Stir in the bath and heat to 190°C for 5 hours. Heating was stopped, the reaction was completed, and left to cool to room temperature. The reaction solution was diluted with water, and a white precipitate precipitated out. Suction filtration, water washing. Then dissolve it with 1,4-dioxane, and then filter while it is hot to remove insoluble impurities. The obtained filtrate was subjected to rotary evaporation under reduced pressure to obtain a light yellow solid, which was then recrystallized from a mixed solvent of methanol and tetrahydrofuran, with a yield of 95%, m.p.>300°C. The structural characterization data of the reaction formula and its products are as follows:

[0026]

[0027] Structural characterization data of the product:

[0028] IR(KBr), σ / cm -1 : 3...

Embodiment 2

[0033] 2-Aminobenzonitrile (0.59g, 0.005mol), DMF (8.0mL), anhydrous zinc chloride (0.67g, 0.005mol), the mixture was added to the autoclave, and then 0.04gCH 3 ONa, stirred in an oil bath and heated to 190°C for 5 hours. Heating was stopped, the reaction was completed, and left to cool to room temperature. The reaction solution was diluted with water, and a white precipitate precipitated out. Suction filtration, water washing. Then dissolve it with 1,4-dioxane, and then filter while it is hot to remove insoluble impurities. The obtained filtrate was rotary evaporated under reduced pressure to obtain a light yellow solid, which was then recrystallized from a mixed solvent of methanol and tetrahydrofuran, with a yield of 93%, m.p.>300°C.

Embodiment 3

[0035] 2-Aminobenzonitrile (0.59g, 0.005mol), DMF (8.0mL), anhydrous copper chloride (0.67g, 0.005mol), the mixture was added to the autoclave, 0.1ml of concentrated hydrochloric acid was added dropwise, oil Stir in the bath and heat to 190°C for 5 hours. Heating was stopped, the reaction was completed, and left to cool to room temperature. The reaction solution was diluted with water, and a white precipitate precipitated out. Suction filtration, water washing. Then dissolve it with 1,4-dioxane, and then filter while it is hot to remove insoluble impurities. The obtained filtrate was rotary evaporated under reduced pressure to obtain a light yellow solid, which was then recrystallized from a mixed solvent of methanol and tetrahydrofuran, with a yield of 78%, m.p.>300°C.

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Abstract

The invention relates to a method for synthesizing 1H,3H-quinazoline-2,4-diketone, belonging to the filed of organic synthesis. The method comprises the following steps: taking o-amino-nitrile as raw materials, catalyzing the raw materials by Lewis acid and protonic acid, condensing the raw materials with N-alkyl formamide, and synthesizing the 1H,3H-quinazoline-2,4-diketone and derivative thereof by one step. The method avoids the use of cyanide (toxic) in the traditional method, and simultaneously improves the productivity to a greater extent.

Description

technical field [0001] The invention relates to a method for synthesizing 1H, 3H-quinazoline-2, 4-dione (English name 1H, 3H-quinazoline-2, 4-diones) compound, which belongs to the field of drug synthesis. Background technique [0002] 1H,3H-quinazoline-2,4-dione heterocyclic compounds have good biological activity and pharmaceutical activity, and are an important class of pharmaceutical and fine chemical intermediates, which can be used in the synthesis of various drugs, such as via 1H , 3H-quinazoline-2,4-dione can synthesize the N-phenyl-1H-quinazoline-2,4-dione compound ( Farmaco, 2001, 56:803-807), synthesized a series of parent ring substances 3-N-ethyl-1-N-(2-nitro) with PDE-4 (phosphodiesterase IV) selective inhibitors -Phenyl-1H,3H-quinazoline-2,4-dione (Eur.J.Med.Chem, 2000,35(5):4632-480); via 7-chloro-1H,3H-quinazole Phenoline-2,4-dione synthesis of FK366 with reductase inhibitors and diabetic complications, And KF31327 (Tetrahedron, 2002, 58:3155), which is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/96
Inventor 李加荣陈霰李英马淑玲李青史大昕
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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