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Method for preparing 1,5-benzothiazine compounds under catalysis action of zirconocene dichloride

A technology of zirconocene dichloride and benzothiazine is applied in the field of efficient preparation of 1,5-benzothiazine compounds, and can solve the problems of lack of diversity synthesis of 1,5-benzothiazine compounds, and the like, Achieve the effect of non-toxic solvent, short time and mild reaction conditions

Active Publication Date: 2019-08-30
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Compared with the stable five-membered ring and six-membered ring structure, researchers have done the least research on the appendages on the seven-membered ring. Therefore, the diversity of 1,5-benzothiazine compounds specialized synthesis is very lacking

Method used

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  • Method for preparing 1,5-benzothiazine compounds under catalysis action of zirconocene dichloride
  • Method for preparing 1,5-benzothiazine compounds under catalysis action of zirconocene dichloride
  • Method for preparing 1,5-benzothiazine compounds under catalysis action of zirconocene dichloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of 2,4-diphenyl-1,5-benzothiazine with the following structural formula

[0018]

[0019] Add 0.103 g (0.5 mmol) 1,4-diphenyl-3-butyne-2-one, 65 μL (0.6 mmol) anthranilobenzenethiol, 0.0074 g (0.025 mmol) zirconocene dichloride to the reaction tube . Dichloromethane volume ratio is the mixed solution of 2:1), obtains 2,4-diphenyl-1,5-benzothiazine, and its productive rate is 97%, and the spectral data of product is: 1 H NMR (400MHz, CDCl 3 )δ8.03(dd, J=6.5,2.9Hz,2H),7.82(d,J=7.3Hz,2H),7.48-7.32(m,9H),7.15(t,J=7.6Hz,1H), 6.85(s,1H); 13 C NMR (101MHz, CDCl 3 )δ165.83, 150.33, 150.07, 139.32, 138.58, 132.82, 130.91, 129.65, 129.41, 128.69, 128.61, 128.15, 127.92, 127.56, 126.69, 126.41, 124.52.

Embodiment 2

[0025] Preparation of 2-(4-chlorophenyl)-4-phenyl-1,5-benzothiazine with the following structural formula

[0026]

[0027] In this example, the 1,4-diphenyl-3-butyne used in Example 1 was replaced with equimolar 1-(4-chlorophenyl)-4-phenyl-3-butyne-2-one -2-ketone, other steps are the same as in Example 1 to obtain 2-(4-chlorophenyl)-4-phenyl-1,5-benzothiazine, the yield is 94%, and the spectral data of the product is : 1 H NMR (400MHz, CDCl 3 )δ7.88(d, J=8.3Hz, 2H), 7.77-7.70(m, 2H), 7.35(dd, J=7.9, 4.9Hz, 3H), 7.29(dd, J=6.9, 4.9Hz, 5H ),7.10(dt,J=8.4,4.3Hz,1H),6.73(s,1H); 13 C NMR (101MHz, CDCl 3 )δ165.92, 151.90, 151.48, 139.80, 139.14, 138.42, 134.21, 131.12, 130.82, 130.59, 130.17, 130.08, 129.32, 128.91, 128.28, 127.77, 125.29.

Embodiment 3

[0029] Preparation of 2-(4-bromophenyl)-4-phenyl-1,5-benzothiazine with the following structural formula

[0030]

[0031] In this example, the 1,4-diphenyl-3-butane used in Example 1 was replaced with an equimolar 1-(4-bromophenyl)-4-phenyl-3-butyn-2-one Alkyne-2-one, other steps are the same as in Example 1, to obtain 2-(4-bromophenyl)-4-phenyl-1,5-benzothiazine, its yield is 91%, the spectral data of the product for: 1 H NMR (400MHz, CDCl 3 )δ7.80(d, J=8.6Hz, 2H), 7.74-7.69(m, 2H), 7.49(d, J=8.5Hz, 2H), 7.35(d, J=7.7Hz, 1H), 7.32- 7.24(m,5H),7.09(dt,J=8.3,4.4Hz,1H),6.71(s,1H); 13 C NMR (101MHz, CDCl 3 )δ166.02, 151.94, 151.48, 139.79, 139.58, 134.22, 133.13, 131.13, 130.83, 130.81, 130.09, 129.31, 128.91, 128.31, 127.76, 126.92, 125.22.

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Abstract

The invention discloses a method for preparing 1,5-benzothiazine compounds under the catalysis action of zirconocene dichloride. According to the method, 3-butyne-2-ketone compounds and o-aminobenzenethiol compounds are taken as raw materials, zirconocene dichloride is taken as a catalyst, and the 1,5-benzothiazine compounds are prepared efficient in a high-yield manner under the promotion actionof ligands such as L-phenylalanine, 3-nitrophthalic acid, 2-aminobenzene sulfonic acid and the like. According to the method, a few catalyst is used and is low in cost, non-toxic and stable to the air, the reaction conditions are mild, short time is consumed, operation is simple, the atom economy is high, all that is required is to perform simple column chromatography isolation on a product afterthe reaction ends, and the 1,5-benzothiazine compounds can be obtained. A novel, low-cost and efficient way is developed for preparation of the 1,5-benzothiazine compounds, and the method has broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of synthesis of 1,5-benzothiazine compounds, in particular to a kind of zirconocene dichloride catalyzing the reaction of 3-butyne-2-one compounds and o-aminobenzenethiol compounds, which can be efficiently prepared 1,5-Benzothiazines method. Background technique [0002] The 1,5-benzothiazine skeleton widely exists in natural products and has been identified as a pleiotropic pharmacophore, and its derivatives include anti-HIV drugs and anti-cancer drugs, angiotensin-converting enzyme inhibitors, antibiotics and antifungal compounds, calmodulin antagonists, and Ca 2+ blockers, etc. In addition, because many 1,5-benzothiazines have antifungal, antibacterial, anti-inflammatory, analgesic and anticonvulsant activities, they are of great significance in medicine and organic synthesis. [0003] Compared with the stable five-membered ring and six-membered ring structure, researchers have done the least research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D281/10C07D417/04
CPCC07D281/10C07D417/04Y02P20/584
Inventor 高子伟杨明明张刊周玉杰孙华明
Owner SHAANXI NORMAL UNIV
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