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A kind of preparation method of benzothiazine compound

A technology of benzothiazine and compounds, which is applied in the field of preparation of benzothiazine compounds, can solve the problems of long reaction time and achieve the effects of short reaction time, simple operation and mild reaction conditions

Active Publication Date: 2019-09-06
江苏泓诺健生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Utilize above-mentioned method to synthesize benzothiazine compound in laboratory, have obvious shortcoming and deficiency: 1) need nitrogen protection; 2) need metal or strong acid catalysis; 3) reaction time is long

Method used

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  • A kind of preparation method of benzothiazine compound
  • A kind of preparation method of benzothiazine compound
  • A kind of preparation method of benzothiazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of compound 3a

[0022]

[0023] Add N-benzylbenzothioamide (0.4mmol, 91mg), hydroxytoluenesulfonyl iodobenzene (0.4mmol, 157mg), and 4.0mL hexafluoroisopropanol into a 15mL thick-walled pressure-resistant tube, and stir at room temperature 10 minutes. After the reaction was completed, 2-phenyl-4,5-dihydro-1,3-benzothiazine 3a was obtained by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=30 / 1) , 74% isolated yield.

[0024] Spectral analysis data 3a:

[0025] 1 H NMR (500MHz, CDCl 3 ):δ8.00(d,J=7.3Hz,2H),7.47-7.37(m,4H),7.33-7.27(m,3H),4.78(s,2H). 13 C NMR (125MHz, CDCl 3 ): δ161.6(s,1C),136.9(s,1C),131.3(s,1C),131.1(s,1C),130.9(s,1C),128.5(s,2C),127.7(s, 2C), 127.5(s, 2C), 126.8(s, 1C), 126.6(s, 1C), 56.7(s, 1C).

Embodiment 2

[0027] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0028]

[0029] Spectrum analysis data 3b:

[0030] 1 H NMR (500MHz, CDCl 3 ):δ7.95(d,J=8.5Hz,2H),7.41-7.38(m,3H),7.34-7.29(m,3H),4.79(s,2H). 13 C NMR (125MHz, CDCl 3 ): δ160.5(s,1C),137.3(s,1C),135.4(s,1C),131.2(s,1C),130.6(s,1C),129.0(s,2C),128.8(s, 2C),127.6(s,2C),126.9(s,1C),126.6(s,1C),56.8(s,1C).HRMS(ESI-TOF,[M+H] + ): calcd for C 14 h 11 NSCl, 260.0301, found 260.0307.

Embodiment 3

[0032] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0033]

[0034] Spectrum analysis data 3c:

[0035] 1 H NMR (500MHz, CDCl 3 ):δ8.12(d,J=8.2Hz,2H),7.69(d,J=8.2Hz,2H),7.41-7.39(m,1H),7.35-7.30(m,3H),4.83(s, 2H). 13 C NMR (125MHz, CDCl 3 ): δ160.4(s,1C),140.1(s,1C),132.7(q,J=32.6Hz,1C),130.8(s,1C),130.3(s,1C),128.0(s,2C) ,127.8(s,1C),127.7(s,1C),126.9(s,1C),126.6(s,1C),125.5(s,2C),123.8(q,J=270.3Hz,1C),56.9( s,1C).HRMS(ESI-TOF,[M+H] + ): calcd for C 15 h 11 f 3 NS, 294.0564, found 294.0571.

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Abstract

The invention discloses a benzothiazine compound preparation method, which belongs to the technical field of organic synthesis. The method is characterized in that thioamide, hydroxy(tosyloxy)iodo benzene, and a solvent are added in a reactor, after the reaction is completed under room temperature, a silica gel column chromatography is used for separating to obtain a pure object product. The preparation method has the characteristics of scientific and reasonable performance, mild condition, simple operation and short reaction time. A reaction equation is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of benzothiazine compounds. Background technique [0002] As an important class of compounds in heterocyclic compounds, benzothiazines have certain physiological activities. Studies have shown that such heterocyclic compounds and their derivatives can be used as anti-tuberculosis drugs (J.Med.Chem.2012,55,7940 ), antitumor drugs (J.Med.Chem.2015,58,6678) and HIV inhibitors (Bioorg.Med.Chem.Lett.2016,26,1738), in view of the wide range of biological activities and It is of great significance to develop a new method for the practical and effective synthesis of benzothiazine compounds. [0003] The preparation method of benzothiazine compound has: [0004] 1) Take o-iodobenzylamine and benzaldehyde as raw materials [0005] The research group used o-iodobenzylamine and benzaldehyde as raw materials, cuprous iodide as catalyst, and tolu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/08C07D417/04C07F9/6547
Inventor 郭维斯周程程文丽荣李明
Owner 江苏泓诺健生物医药科技有限公司
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