Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules

A technology of trifluoromethyl and quinazolinone, which is applied in the field of organic synthesis, can solve the problems of expensive reaction substrates, harsh reaction conditions, and narrow substrate range, and achieve simple post-treatment, easy operation, and high reaction efficiency Effect

Active Publication Date: 2021-06-29
ZHEJIANG POLICE COLLEGE
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Problems solved by technology

The synthetic methods mentioned above are generally limited by the harsh reaction conditions, the reactio

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  • Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules
  • Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules
  • Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules

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Embodiment Construction

[0032] The present invention will be further described below in conjunction with specific embodiments.

[0033] Add palladium trifluoroacetate, triphenylphosphine, TFBen, sodium carbonate, trifluoroethylimidoyl chloride (II), amine (III) and 2 mL of organic solvent into a 35 mL Schlenk tube according to the raw material ratio in Table 1, and mix Stir evenly, react for 16-30 hours according to the reaction conditions in Table 2, filter, mix the sample with silica gel, obtain the corresponding 2-trifluoromethyl-substituted quinazolinone compound (I) through column chromatography purification, and the reaction process is as follows: Shown:

[0034]

[0035] The raw material addition of table 1 embodiment 1~15

[0036]

[0037] Table 2

[0038]

[0039]

[0040] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Bn is benzyl, Me is methyl, OMe is methoxy, n-Bu is n-butyl, t-Bu is tert-butyl, i-Pr is isopropyl, Cy is cyclohex...

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Abstract

The invention discloses a preparation method of a 2-trifluoromethyl substituted quinazolinone compound. The preparation method comprises the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, trifluoroethylimido acyl chloride and amine into an organic solvent, reacting at 110 DEG C for 16-30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted quinazolinone compound. The preparation method has the advantages of simple operation, cheap and easily available initial raw materials, high reaction efficiency, good substrate compatibility, synthesis of trifluoromethyl quinazolinone compounds substituted by different groups through substrate design, convenient operation, and broadening of the practicality of the method. The method is also successfully applied to the high-yield synthesis of the drug molecule Rutaecarpine.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of a 2-trifluoromethyl-substituted quinazolinone compound and an application of the method in synthesizing drug molecules. Background technique [0002] Quinazolinone compounds are an important fused-ring nitrogen-containing six-membered heterocycle, which widely exist in various natural products and drug molecules, and have a series of biological and pharmaceutical activities, such as antifungal, antibacterial, antiviral, anti Inflammatory, anticonvulsant and anticancer properties (Eur. J. Med. Chem., 2015, 90, 124). Many common drugs on the market contain quinazolinone molecular structures, such as fluoroquinone, methaqualone, methylchloroquinone and benzaliquinone. The introduction of trifluoromethyl groups into heterocyclic molecules can significantly improve the physicochemical properties of the parent molecule, such as electronegativity, bi...

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Application Information

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IPC IPC(8): C07D239/90C07D239/91C07D471/14
CPCC07D239/90C07D239/91C07D471/14
Inventor 王斌杰俞逸娴陈铮凯吴元钊姚伟宣王继业
Owner ZHEJIANG POLICE COLLEGE
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