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Synthesis method of triazole benzothiazinone fused heterocycle

A synthesis method and benzothiazine technology are applied in the synthesis field of triazole benzothiazinone fused heterocycles, can solve problems such as difficulty in obtaining starting materials, and achieve the effect of mild reaction conditions

Active Publication Date: 2015-07-22
陈定奔 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And above-mentioned reaction method starting material is difficult to obtain

Method used

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  • Synthesis method of triazole benzothiazinone fused heterocycle
  • Synthesis method of triazole benzothiazinone fused heterocycle
  • Synthesis method of triazole benzothiazinone fused heterocycle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: In a Schlenk reaction tube, 2-iodobenzoic acid (0.5 mmol), 3-mercapto-1,2,4-triazole (0.5 mmol), potassium carbonate (0.1 mmol) and HMPA (2 mL) were added. The reaction tube was sealed, and the reaction was carried out at 80° C. for 24 hours in an air atmosphere. After the reaction, glacial acetic acid (1ml) was added, stirred at room temperature for 1 hour, then extracted three times with dichloromethane, and the organic layer was washed three times with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Utilize column chromatography to separate and purify, obtain product 1, its structure and characterization data are as follows:

[0019]

[0020] 9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-one(1)an white solid(92.5mg,91%), m.p.211-213℃; 1 H NMR (500MHz, CDCl 3 / TMS): δ: 8.69 (dd, J = 8.0, 1.0Hz, 1H), 8.33 (s, 1H), 7.80-7.79 (m, 1H), 7.66-7.64 (m, 2H) ppm; 13 C NMR (125MHz, CDCl 3 / TMS): δ: 155.9, 153.5, 15...

Embodiment 2

[0021] Example 2: In the Schlenk reaction tube, add 5-methyl-2-iodobenzoic acid (0.5mmol), 3-mercapto 1,2,4-triazole (0.5mmol), potassium carbonate (0.1mmol) and HMPA (2 mL). The reaction tube was sealed, and the reaction was carried out at 80° C. for 24 hours in an air atmosphere. After the reaction, acetic acid (1ml) was added, stirred at room temperature for 1 hour, then extracted three times with dichloromethane, the organic layer was washed three times with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Utilize column chromatography to separate and purify, obtain product 2, its structure and characterization data are as follows:

[0022]

[0023] 7-Methyl-9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-one(2)an white solid(96.7mg,89%),m.p.223-225℃ ; 1 H NMR (500MHz, CDCl 3 / TMS): δ:8.49(d,J=0.5Hz,1H),8.30(s,1H),7.60(dd,J=8.0,1.5Hz,1H),7.53(d,J=8.5Hz,1H) ,2.52(s,3H)ppm; 13 C NMR (125MHz, CDCl 3 / TMS):δ:156.0,153.5,151....

Embodiment 3

[0024] Embodiment 3: in the Schlenk reaction tube, add 5-chloro-2-iodobenzoic acid (0.5mmol), 3-mercapto 1,2,4-triazole (0.5mmol), potassium carbonate (0.1mmol) and HMPA ( 2mL). The reaction tube was sealed, and the reaction was carried out at 80° C. for 24 hours in an air atmosphere. After the reaction, acetic acid (1ml) was added, stirred at room temperature for 1 hour, then extracted three times with dichloromethane, the organic layer was washed three times with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Utilize column chromatography to separate and purify, obtain product 3, its structure and characterization data are as follows:

[0025]

[0026] 7-Chloro-9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-one(3)an white solid(95.1mg,80%),m.p.248-250℃ ; 1 H NMR (500MHz, CDCl 3 / TMS): δ: 8.67(d, J=2.0Hz, 1H), 8.34(s, 1H), 7.76(dd, J=8.5, 2.5Hz, 1H), 7.62(d, J=8.5Hz, 1H) ppm; 13 C NMR (125MHz, CDCl 3 / TMS):δ:154.9,153.9,...

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Abstract

The invention relates to a synthesis method of a triazole benzothiazinone fused heterocycle and in particular to a synthesis method of 9H-[1,2,4]triazole-[5,1-b][1,3]-benzothiazinone-9-ketone. The method is characterized by enabling substituted 2-halogen benzoic acid and substituted 2-sulfydryl triazole heterocycle which serve as the raw materials to carry out C-S coupling / condensation amidation one-pot reaction in a solvent in the absence of a metal catalyst to synthesize corresponding products. The method is simple and convenient to operate, easily available in raw materials and high in efficiency. The method is a novel synthesis method of 9H-[1,2,4]triazole-[5,1-b][1,3]-benzothiazinone-9-ketone.

Description

technical field [0001] The present invention relates to a synthesis method of triazole benzothiazinone condensed heterocyclic ring, in particular to 9 hydrogen-[1,2,4]triazole-[5,1-b][1,3]-benzene Synthetic method of thiazin-9-one. Background technique [0002] Organosulfur compounds are widely found in pharmaceuticals and natural products. Therefore, the formation of carbon-sulfur bonds is an important reaction in organic synthesis. Over the past few decades, transition metal catalysis has become an important tool for building C-S bonds (Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. Beletskaya, I.P.; Ananikov, V.P. 111, 1596. Lee, C.; Liu, Y.; Badsara, S.S. Chem. Asian J. 2014, 9, 706.). Transition metal catalysts, such as palladium, ruthenium, rhodium, copper, and iron catalysts, catalyze the formation of carbon-sulfur bonds with high efficiency. However, transition metal catalysis can easily cause catalyst poisoning, thereby reducing the reaction efficiency. The...

Claims

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Application Information

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IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 陆加明陈定奔黄凌
Owner 陈定奔
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