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Preparation method of 2-trifluoromethyl substituted quinazolinone derivative

A technology of trifluoromethyl and quinazolinone, which is applied in the field of preparation of quinazolinone derivatives, can solve the problems of harsh reaction conditions, expensive reaction substrates, narrow substrate range, etc., and achieve good substrate applicability , Strong designability and high reaction efficiency

Pending Publication Date: 2020-12-25
ZHEJIANG SCI-TECH UNIV
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  • Abstract
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Problems solved by technology

The synthetic methods described above generally have the following disadvantages, such as harsh reaction conditions, expensive reaction substrates or pre-activation, low yields, and narrow substrate ranges.

Method used

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  • Preparation method of 2-trifluoromethyl substituted quinazolinone derivative
  • Preparation method of 2-trifluoromethyl substituted quinazolinone derivative
  • Preparation method of 2-trifluoromethyl substituted quinazolinone derivative

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Embodiment Construction

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

[0033] Add ditriphenylphosphinepalladium dichloride, 1,3-bis(diphenylphosphine)propane, TFBen, potassium tert-butoxide, and o-iodoaniline (II) into a 35mL Schlenk tube according to the raw material ratio in Table 1 , trifluoroethylimidoyl chloride (III) and organic solvent 2mL, mixed and stirred evenly, reacted for 16-30 hours according to the reaction conditions in Table 2, filtered, mixed with silica gel, and purified by column chromatography to obtain the corresponding 2-trifluoro Methyl-substituted quinazolinone derivatives (I), the reaction process is shown in the following formula:

[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, naphthyl is naphthyl, Me is methyl, t-Bu is tert-butyl, t-Bu...

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Abstract

The invention discloses a preparation method of a 2-trifluoromethyl substituted quinazolinone derivative, which comprises the following steps of: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, trifluoroethyl imine acyl chloride and o-iodobenzidine into an organic solvent, reacting at 90 DEG C for 16-30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted quinazolinone derivative. The preparation method has the advantages of simple operation, cheap and easily available reaction starting raw materials, compatibility with a plurality of substituents, good substrate applicability, realization of synthesis of trifluoromethyl quinazolinone derivatives substituted by different groups through substrate design, convenience in operation, and higher practicality. According to the method, 1, 3, 5-triformic acid phenol ester is used as a solid carbon monoxide substitute, so that the use of toxic and colorless gas carbon monoxide is avoided.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of 2-trifluoromethyl-substituted quinazolinone derivatives. Background technique [0002] Quinazolinone derivatives are important fused-ring nitrogen-containing six-membered heterocycles, which widely exist in various natural products and drug molecules, and have a spectrum of biological and pharmaceutical activities, such as anti-inflammatory, anti-viral, anti-fungal, Anticonvulsant and anticancer properties (Eur.J.Med.Chem., 2015, 90, 124). Many commercially available drugs contain quinazolinone molecular skeletons, such as fluoroquinone, methaqualone, methylchloroquinone and benzaliquinone. Due to the special properties of the fluorine atom, the introduction of trifluoromethyl into the molecule can significantly improve the physical and chemical properties of the parent molecule, such as electronegativity, bioavailability, metabolic stability and lipophil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91
CPCC07D239/91
Inventor 吴小锋陈铮凯杨合肥
Owner ZHEJIANG SCI-TECH UNIV
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