Thiazine derivative and synthetic method thereof

A synthesis method and derivative technology, applied in the direction of organic chemistry, can solve environmental pollution and other problems, and achieve the effects of environmental friendliness, cheap catalyst, and convenient post-treatment

Inactive Publication Date: 2017-08-18
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
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Problems solved by technology

Therefore, the synthesis methods of many thiazides have been reported in the literature, most of which are through the nucleophilic addition of sulfur atoms in the molecule to carbon-carbon triple bonds to form thiazine rings, such as the synthesis of thiazide compounds under metal catalysis, such as : (1) L. Hua, Zh

Method used

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  • Thiazine derivative and synthetic method thereof
  • Thiazine derivative and synthetic method thereof
  • Thiazine derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0029] Example 1: Synthesis of cis-6-benzylidene-2-phenyl-6H-1,3-thiazine-5-carboxylic acid ethyl ester

[0030]

[0031] The thiobenzamide group-substituted enynyl ester, DABCO, and solvent are respectively selected: trans-4-phenyl-2-(phenylthioiminomethylene) ethyl but-3-ynoate, DABCO, chlorine Benzene, the raw material dosage is trans-4-phenyl-2-(phenylthioiminomethylene)but-3-ynoic acid ethyl ester 0.2mmol, DABCO 1mmol, chlorobenzene 2ml. The reaction was carried out at 110°C for 22 hours to obtain the target product as a brown liquid with an isolated yield of 90%.

[0032] NMR data: 1 H NMR(400MHz, CDCl 3 )δ1.39(t,J=7.2Hz,3H),4.36(q,J=6.8Hz,2H),7.26-7.34(m,2H),7.36-7.47(m,6H),7.49-7.56(m ,1H),7.95(d,J=7.6Hz 2H),8.00(s,1H); 13 C NMR(100MHz, CDCl 3 )δ13.94,61.29,114.74,119.89,127.72,128.26,128.39,128.90,129.43,129.84,132.87,135.68,136.79,145.04,166.20,166.69;

[0033] High resolution mass spectrum data: HRMS(EI)calcd for C 20 H 17 NO 2 S: 335.0980, found 336.1057.

Example Embodiment

[0034] Example 2: Synthesis of cis-6-benzylidene-2-phenyl-6H-1,3-thiazine-5-carboxylic acid ethyl ester

[0035]

[0036] Thiobenzamide group substituted enynyl ester, K 2 CO 3 , Solvent selection: trans-4-phenyl-2-(phenylthioiminomethylene) ethyl but-3-ynoate, K 2 CO 3 , Chlorobenzene, the raw material dosage is trans-4-phenyl-2-(phenylthioiminomethylene)but-3-ynoic acid ethyl ester 0.2mmol, K 2 CO 3 2.0mmol, 2ml chlorobenzene. The reaction was carried out at 110°C for 24 hours to obtain the target product as a brown liquid with an isolated yield of 50%.

[0037] NMR data: 1 H NMR(400MHz, CDCl 3 )δ1.39(t,J=7.2Hz,3H),4.36(q,J=6.8Hz,2H),7.26-7.34(m,2H),7.36-7.47(m,6H),7.49-7.56(m ,1H),7.95(d,J=7.6Hz 2H),8.00(s,1H); 13 C NMR(100MHz, CDCl 3 )δ13.94,61.29,114.74,119.89,127.72,128.26,128.39,128.90,129.43,129.84,132.87,135.68,136.79,145.04,166.20,166.69;

[0038] High resolution mass spectrum data: HRMS(EI)calcd for C 20 H 17 NO 2 S: 335.0980, found 336.1057.

Example Embodiment

[0039] Example 3: Synthesis of cis-6-benzylidene-2-phenyl-6H-1,3-thiazine-5-carboxylic acid ethyl ester

[0040]

[0041] The thiobenzamide group-substituted enynyl ester, DABC, and solvent are respectively selected: trans-4-phenyl-2-(phenylthioiminomethylene) ethyl but-3-ynoate, DABCO, chlorine Benzene, the raw material dosage is 0.2mmol of trans-4-phenyl-2-(phenylthioiminomethylene)but-3-ynoic acid ethyl ester, DABCO 0.04mmol, and toluene 2ml. The reaction was carried out at 80°C for 34 hours to obtain the target product as a brown liquid with an isolated yield of 75%.

[0042] NMR data: 1 H NMR(400MHz, CDCl 3 )δ1.39(t,J=7.2Hz,3H),4.36(q,J=6.8Hz,2H),7.26-7.34(m,2H),7.36-7.47(m,6H),7.49-7.56(m ,1H),7.95(d,J=7.6Hz 2H),8.00(s,1H); 13 C NMR(100MHz, CDCl 3 )δ13.94,61.29,114.74,119.89,127.72,128.26,128.39,128.90,129.43,129.84,132.87,135.68,136.79,145.04,166.20,166.69;

[0043] High resolution mass spectrum data: HRMS(EI)calcd for C 20 H 17 NO 2 S: 335.0980, found 336.1057.

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Abstract

The invention discloses a thiazine derivative as shown in a formula (I) and a synthetic method thereof. The thiazine derivative as shown in the formula (I) is synthesized from a sulfamide substituted eneyne ester compound in the presence of a catalyst. The preparation method disclosed by the invention has the advantages of simple and easily available raw materials, simple post-treatment, no metal catalysts, good yield, environmental-friendly effect and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and relates to base-catalyzed thiazine derivatives and a synthesis method thereof. Background technique [0002] Thiazide compounds are relatively important organic compounds, which are the intermediate components of many substances and are of great significance to human beings. Most of it exists in medicines, pesticides, dyes, natural active products and synthetic materials, and can also be used as intermediates in organic synthesis, and has great value in the synthesis of medicines and materials. These related fields have attracted the attention of synthetic, medical, and materials scientists. Therefore, many synthetic methods of thiazides have been reported in the literature, most of which are formed by nucleophilic addition of sulfur atoms in the molecule to carbon-carbon triple bonds to form thiazine rings, such as the synthesis of thiazide compounds under metal cata...

Claims

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Application Information

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IPC IPC(8): C07D279/06
CPCC07D279/06
Inventor 李艳忠陶相华周圆圆姚其义孔令凯赵育磊郑重袁洋王孟丹徐穆榕张芳芳
Owner EAST CHINA NORMAL UNIVERSITY
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