Preparation method of 2-trifluoromethyl substituted quinazolinone compound

A quinazolinone and trifluoromethyl technology, applied in the field of organic synthesis, can solve the problems of severe reaction conditions, expensive reaction substrates, narrow substrate range, etc., and achieve high reaction efficiency, strong designability, and post-treatment convenient effect

Active Publication Date: 2020-09-18
ZHEJIANG SCI-TECH UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

Among them, the more commonly used trifluoromethyl synthons are trifluoroacetic anhydride and ethyl trifluoroacetate. The above-mentioned synthetic methods are generally limited by severe reaction conditions, expensive reaction substrates, low yields, and narrow substrate ranges. shortcoming

Method used

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

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Embodiment Construction

[0033] The present invention will be further described below in conjunction with specific embodiments.

[0034] Add ferric chloride, sodium hydrogen, Molecular sieves, trifluoroethylimidoyl chloride (II), isatin (III) and 2 mL of organic solvent, mixed and stirred evenly, reacted for 24-48 hours according to the reaction conditions in Table 2, filtered, mixed with silica gel, purified by column chromatography Obtain the corresponding 2-trifluoromethyl substituted quinazolinone compound (I), and the reaction process is shown in the following formula:

[0035]

[0036] The raw material addition of table 1 embodiment 1~11

[0037]

[0038] Table 2

[0039]

[0040]

[0041] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, OMe is methoxy, NO 2 for nitro, R F Trifluoromethyl, DMF is N,N-dimethylformamide. The structural confirmation data of the compounds prepared in Examples 1-5:

[0042] The nuclear magne...

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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 ferric trichloride, sodium hydrogen, a molecular sieve, trifluoroethyleneimide chloride and isatin into an organic solvent, reacting at the temperature of 40 DEG C for 10 hours, heating to 120 DEG C, reacting for 20 hours, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted quinazolinone compound. The preparation method is simple and convenient to operate, cheap and easily available in initial raw materials and catalysts, high in reaction efficiency and wide in substrate compatibility range, diversified substituted quinazolinone compounds with trifluoromethyl can be synthesized through substrate design, and the practicability of the method is widened while operation is facilitated.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a 2-trifluoromethyl-substituted quinazolinone compound. Background technique [0002] Quinazolinone compound is an important nitrogen-containing fused six-membered heterocyclic ring, which widely exists in various molecular frameworks with important biological activities (Bioorg. Med. Chem. 2016, 24, 2361-2381). Many natural products and drug molecules contain quinazolinone molecular structures. They generally have anticancer, anticonvulsant, antiinflammatory, antifungal and antimalarial activities (Eur. J. Med. Chem. 2015, 90, 124-169). The introduction of trifluoromethyl groups into specific heterocyclic molecules has many advantages, which can significantly improve the electronegativity, bioavailability, metabolic stability and lipophilicity of target molecules (J.Med.Chem.2015,58, 8315-8359) . [0003] [0004] The methods for synthesizing quinaz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/90
CPCC07D239/90
Inventor 吴小锋陈铮凯王乐程
Owner ZHEJIANG SCI-TECH UNIV
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