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

A technology for synthesizing quinazoline and amine compounds, applied in the direction of organic chemistry and the like, can solve the problems of poor step economy and atom economy, harsh reaction conditions, single raw material structure, etc., and achieves high atom economy and step economy, The effect of mild reaction conditions and simple raw material structure

Active Publication Date: 2020-12-18
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although many synthetic methods have been developed, there are still many deficiencies in these synthetic methods to varying degrees, such as, the structure of the raw materials used is complex, the types are limited, the source is inconvenient, and the cost is high; the structure of the raw materials is sing

Method used

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

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Embodiment

[0011] Synthesis of quinazoline-2,4(1H,3H)-dione under different conditions in Table 1 a

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[0014]

[0015] a Reaction conditions: N-methylanthranilic acid (1.0mmol), butylamine (3.0mmol), copper acetate (1.0mmol), palladium acetate (5mol%), potassium iodide (0.2mmol), acetonitrile (10.0mL), reaction After 6 hours additional CO was sparged. b Separation yield. c Butylamine was added dropwise. d Butylamine and acetic acid (1.0 mmol) were added dropwise. e Butylamine and acetic acid (1.0 mmol) were added after 6 hours. f CO:O 2 =5:1, v / v. g Butylamine and acetonitrile were added after 6 hours. Substrate expansion of N-substituted anthranilic acid compounds:

[0016] Table 2N-substituted anthranilic acid substrate scope a

[0017]

[0018]

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[0020]

[0021] a Reaction conditions: N-substituted anthranilic acid compound (1.0mmol), butylamine (3.0mmol), copper acetate (1.0mmol), palladium acetate (5mol%), potassium iodide (...

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Abstract

The invention discloses a method for synthesizing a quinazoline-2, 4 (1H, 3H)-diketone compound, and belongs to the technical field of synthesis of nitrogen-containing heterocyclic compounds. According to the technical scheme, the method is characterized in that an anthranilic acid compound and an amine compound serve as reaction raw materials, CO serves as a carbonylation reagent, Pd (II) servesas a catalyst, KI or KI/AcOH serves as an additive, Cu (OAc) 2 or O2 or Cu (OAc) 2/O2 serves as an oxidizing agent, and the target product quinazoline-2, 4 (1H, 3H)-diketone compound is prepared through a one-pot multi-component reaction. The method has the advantages of simple and easily available raw material, short synthesis route, high atom economy and step economy, mild reaction conditions, diversified product structures, high yield of most target products and the like.

Description

technical field [0001] The invention belongs to the technical field of synthesis of nitrogen-containing heterocyclic compounds, and in particular relates to a method for synthesizing quinazoline-2,4(1H,3H)-dione compounds. Background technique [0002] Quinazoline-2,4(1H,3H)-dione compounds are common nitrogen-containing heterocyclic compounds. Because of their wide range of pharmaceutical activities, they have attracted extensive attention from researchers in the fields of biology, chemistry and medicine. There are many uses in medicine, pesticides and organic synthesis, for example: in medicine, it can be used as anticancer drugs, antibacterial drugs, antispasmodic and anticonvulsant drugs, antihypertensive drugs, anti-inflammatory drugs, antidiabetic drugs and some Other medicinal value, etc.; in terms of pesticides, it can be used as herbicides, insecticides and fungicides; it also has important applications in the field of organic synthesis. [0003] The main synthetic...

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Application Information

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IPC IPC(8): C07D239/96C07D401/12C07D417/12
CPCC07D239/96C07D401/12C07D417/12
Inventor 张晓鹏丁前前王近军杨静逸范学森张贵生
Owner HENAN NORMAL UNIV