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A kind of 2-thioquinazolone compound and its preparation method and application

A technology for thioquinazolones and compounds, applied in the field of 2-thioquinazolones and their preparation, capable of solving problems such as cumbersome operations and complicated process routes

Active Publication Date: 2022-06-21
西藏贝斯特药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Yet above-mentioned preparation method process route is complicated, and operation is loaded down with trivial details

Method used

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  • A kind of 2-thioquinazolone compound and its preparation method and application
  • A kind of 2-thioquinazolone compound and its preparation method and application
  • A kind of 2-thioquinazolone compound and its preparation method and application

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preparation example Construction

[0031] The invention provides a kind of preparation method of 2-thioquinazolone compound, it is characterized in that, comprises the following steps:

[0032] Mix anthranilamide, isothiocyanate compound, bromide and polar organic solvent, and carry out a series cyclization reaction under air atmosphere to obtain 2-thioquinazolinone compound;

[0033]

[0034] Among them, R 1 includes hydrogen, alkyl, alkoxy, halogen or heteroatom;

[0035] R 2 Including phenyl, naphthyl, benzoyl, alkyl substituted phenyl, alkoxy substituted phenyl, halogen substituted phenyl, haloalkyl substituted phenyl, nitro substituted phenyl, nitrile substituted phenyl, alkyl, Cycloalkyl or ester groups;

[0036] R 3 Including ester, phenyl, alkenyl or alkynyl.

[0037] In the present invention, unless otherwise specified, all raw material components are commercially available products well known to those skilled in the art.

[0038] In the present invention, the anthranilamide compounds include ...

Embodiment 1

[0057] Add 0.15 mmol of 2-amino-3-methylbenzamide, 0.1 mmol of phenyl isothiocyanate, 0.3 mmol of ethyl bromoacetate, 1.0 mL of acetonitrile into the reaction tube, heat to 80°C, and stir for 12 hours. After the reaction, it was separated and purified by column chromatography, the eluent was petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate in the eluent was 5:1, and the compound having the formula I-1 was obtained. Structured 2-thioquinazolinones (70% yield, 99.9% purity).

[0058] The structure of the obtained product is characterized, and the structural characterization data are as follows:

[0059] 1 H NMR (400MHz, CDCl 3 ,ppm)δ8.10-8.08(d,J=8Hz,1H),7.59-7.55(m,4H),7.38-7.36(q,J=4Hz,2H),7.32-7.28(t,J=8Hz, 1H), 4.24-4.18 (q. J = 8Hz, 2H), 3.89 (s, 2H), 2.57 (s, 3H), 1.30-1.26 (t, J = 8Hz, 3H).

[0060] 13 C{ 1 H}NMR (100MHz, CDCl 3 , ppm) δ168.5, 162.0, 154.8, 146.1, 135.7, 135.3, 134.8, 130.2, 129.8, 129.2, 125.7, 124.9, 119...

Embodiment 2

[0063] Add 0.15 mmol of 2-amino-4-methylbenzamide, 0.1 mmol of phenylisothiocyanate, 0.3 mmol of ethyl bromoacetate, and 1.0 mL of acetonitrile into the reaction tube, heat to 80°C, and stir for 12 hours. After the reaction is finished, it is separated and purified by column chromatography, and the eluent is petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate in the eluent is 5:1, and the compound having the formula I-2 is obtained. Structured 2-thioquinazolinones (yield 68%, purity 99.9%).

[0064] The structure of the obtained product is characterized, and the structural characterization data are as follows:

[0065] 1 H NMR (400MHz, CDCl 3 , ppm) δ8.12-8.10(d, J=8Hz, 1H), 7.56-7.54(t, J=8Hz, 3H), 7.37-7.35(q, J=4Hz, 3H), 7.23-7.21(d, J=8Hz, 1H), 4.25-4.20 (q, J=8Hz, 2H), 3.88(s, 2H), 1.32-1.28 (t, J=8Hz, 3H).

[0066] 13 C{ 1 H}NMR (100MHz, CDCl 3 , ppm) δ168.7, 161.7, 155.9, 147.6, 145.7, 135.7, 130.1, 129.8, 129.2, 127.7, 127...

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PUM

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Abstract

The invention provides a 2-thioquinazolinone compound and its preparation method and application, belonging to the technical field of organic synthesis. The invention provides a preparation method, comprising the following steps: mixing anthranilamide compounds, isothiocyanate compounds, brominated compounds and polar organic solvents, and performing a series cyclization reaction in an air atmosphere to obtain 2-sulfur Substituted quinazolinone compounds. The preparation method provided by the invention can prepare 2-thioquinazolinone compounds in one step without adding a catalyst, the yield and purity of the product are high, the reaction route is simple, the operation is simple, and it is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a 2-thioquinazolinone compound and its preparation method and application. Background technique [0002] Quinazolines are one of the important nitrogen-containing heterocycles, which have significant biological activity and exist in many natural products. The outstanding pharmacological effects of quinazolinones are manifested in analgesic, anti-inflammatory, anticonvulsant, sedative-hypnotic, antihistamine, antihypertensive, anticancer, antimicrobial, antituberculosis and antiviral activities, and have received widespread attention. [0003] Prior art "Synthesis, molecular modeling and anti-cancer evaluation of aseries of quinazoline derivatives" (see Ahmed I.Khodair, Mona A.Alsafi, MohamedS.Nafie.Synthesis, molecular modeling and anti-cancer evaluation of a series of quinazoline derivatives[ J].Carbohydrate Research, 2019, 486 (C): 107832.) discloses a synthetic meth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/95A61P25/04A61P29/00A61P25/08A61P25/20A61P37/08A61P9/12A61P35/00A61P31/00A61P31/06A61P31/12
CPCC07D239/95A61P25/04A61P29/00A61P25/08A61P25/20A61P37/08A61P9/12A61P35/00A61P31/00A61P31/06A61P31/12
Inventor 郑绿茵谢桢郭维吴勇权
Owner 西藏贝斯特药业有限公司
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