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3, 4-dihydro-2H-1, 3-thiazine derivative and preparation method thereof

A technology of -2H-1 and thiazines, applied in organic chemistry, resistance to vector-borne diseases, etc., can solve the problems of few reports on the synthesis of thiazides, and achieve the effects of high yield, simple and efficient method, and convenient post-processing

Active Publication Date: 2020-10-30
SHENZHEN POLYTECHNIC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few reports on the synthesis of thiazine, and most of the existing synthesis focuses on buprofezin or benzothiazine

Method used

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  • 3, 4-dihydro-2H-1, 3-thiazine derivative and preparation method thereof
  • 3, 4-dihydro-2H-1, 3-thiazine derivative and preparation method thereof
  • 3, 4-dihydro-2H-1, 3-thiazine derivative and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0023] The reaction formula of Example 1, the specific structures of compounds III-1, II-1 and product I-1 used are as follows

[0024]

[0025] The specific experimental steps are: 42 mg (0.20 mmol, 1.0 equivalent) of compound III-1 and 57 mg (0.14 mmol, 0.7 equivalent) of compound II-1 were dissolved in 2 mL of dichloroethane, and reacted at 60° C. for 24 hours. After the reaction was completed, the reaction mixture was rotary evaporated under reduced pressure with a water pump to remove the solvent dichloroethane. Residue with 200-300 mesh silica gel, eluent (volume ratio V 石油醚 :V 乙酸乙酯 =20:1~5:1) column chromatography to obtain the compound shown in I-1, and its product was identified by NMR (hydrogen spectrum, carbon spectrum) and high-resolution mass spectrometry.

[0026] Product Ⅰ-1 was a yellow solid with a yield of 91%. 1 H NMR (400MHz, CDCl 3 )δ7.84(dd, J=8.4,1.2Hz,2H),7.56(t,J=7.2Hz,1H),7.46(t,J=7.6Hz,2H),7.13(d,J=8.0Hz, 2H), 7.04(d, J=8.4Hz, 2H), 4.97(s, 2H...

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to a 3, 4-dihydro-2H-1, 3-thiazine derivative and a preparation method thereof. The structural formula of the 3, 4-dihydro-2H-1, 3-thiazine derivative is shown in the specification, and the preparation method of the 3, 4-dihydro-2H-1, 3-thiazine derivative comprises the following steps: taking alpha-enol dithioesterand 1, 3, 5-triazine as initial raw materials, taking dichloroethane as a reaction solvent, and simply and efficiently synthesizing the thiazine derivative at 60 DEG C in one step. According to the method, a precious metal catalyst is not used in the reaction, the reaction operation is simple, the post-treatment is convenient, the yield is generally very high, and inert gas protection is not needed in the preparation process.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to 3,4-dihydro-2H-1,3-thiazine derivatives and a preparation method thereof. Background technique [0002] Organosulfur compounds have shown more and more extensive application prospects in medicine, pesticides, biology, and organic functional materials. As an important class of organosulfur compounds, sulfur-containing heterocyclic rings are important intermediates in the synthesis of many biological and pharmaceutical active molecules, especially the active molecules modified by functional groups usually have potential biological activities. Among them, thiazide compounds are an important branch of sulfur-containing heterocyclic compounds. Studies have found that thiazide and its derivatives have high pharmacological and biological activities, and their traditional medicinal properties are antihistamine and mental stability. . For example, promethazine hydrochloride ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/06C07D417/06
CPCC07D279/06C07D417/06Y02A50/30
Inventor 程斌李慧张昕平贺一轩汪太民翟宏斌孙海燕
Owner SHENZHEN POLYTECHNIC
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