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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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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.-G. Yao, F. Xu and Q. Shen, RSC Adv., 2014, 4, 3113. (2) R.-Y. Tang, et al Synlett, 2010, 1345 (3) G.-Y.Sh.Q, Y.Hu, Q.-P.Ding, Y.-Y.Peng, X.-Zh.Huand J.Wu, Chem.Commun., 2011, 47, 9708 .However, most of the reported methods for synthesizing thiazides use metal catalysis, causing certain pollution to the environment

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

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

[0030]

[0031] Thiobenzamido-substituted enynyl esters, DABCO, and solvents are selected respectively: trans-4-phenyl-2-(phenylthioiminomethylene) but-3-ynoic acid ethyl ester, DABCO, chlorine Benzene, the amount of raw materials used is trans-4-phenyl-2-(phenylthioiminomethylene) but-3-ynoic acid ethyl ester 0.2mmol, DABCO 1mmol, chlorobenzene 2ml. React 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 spectrometry data: HRMS(EI)calcd for C 20 h 17 NO 2 S: 335...

Embodiment 2

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

[0035]

[0036] Thiobenzamido-substituted enynyl esters, K 2 CO 3 , The solvent is selected respectively: trans-4-phenyl-2-(phenylthioiminomethylene) but-3-ynoic acid ethyl ester, K 2 CO 3 , Chlorobenzene, raw material consumption is trans-4-phenyl-2-(phenylthioiminomethylene) but-3-ynoic acid ethyl ester 0.2mmol, K 2 CO 3 2.0mmol, chlorobenzene 2ml. React 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 spectrometry data: HRMS(EI)calcd for C 20 h 17 NO 2 S:...

Embodiment 3

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

[0040]

[0041] Thiobenzamido-substituted enynyl esters, DABCO, and solvents are selected respectively: trans-4-phenyl-2-(phenylthioiminomethylene) but-3-ynoic acid ethyl ester, DABCO, chlorine Benzene, the amount of raw materials used is trans-4-phenyl-2-(phenylthioiminomethylene) but-3-ynoic acid ethyl ester 0.2mmol, DABCO 0.04mmol, toluene 2ml. React 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 spectrometry data: HRMS(EI)calcd for C 20 h 17 NO 2 S: 335.098...

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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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