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A kind of synthetic method of benzo[1,3]-tetrahydrothiazine derivative

A synthesis method, tetrahydrothiazine technology, applied in the field of synthesis of benzo[1,3]-tetrahydrothiazine derivatives, can solve problems such as complicated operation, harsh reaction conditions, high toxicity of reaction raw materials, etc. High efficiency, mild reaction conditions, and good functional group diversity

Active Publication Date: 2021-04-27
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] Although benzo[1,3]-tetrahydrothiazine derivatives (J.Org.Chem.2008,73,1612-1615) can be efficiently prepared by reacting 2-mercaptobenzylamine with phosgene or carbon monoxide, there is a reaction The disadvantages of high toxicity of raw materials, complicated operation and harsh reaction conditions limit the application of these methods

Method used

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  • A kind of synthetic method of benzo[1,3]-tetrahydrothiazine derivative
  • A kind of synthetic method of benzo[1,3]-tetrahydrothiazine derivative
  • A kind of synthetic method of benzo[1,3]-tetrahydrothiazine derivative

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Experimental program
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Embodiment 1

[0028]

[0029] In a 10 mL test tube, N,S-ketal derivative 2a (0.5 mmol), copper bromide (1.5 mmol), lithium bromide (1.5 mmol) and 2.5 mL of toluene were sequentially added under air, and stirred at 110°C for 16 hours. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1 ), the target product 1a was obtained as a yellow solid with a yield of 76%. The target product 1a was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0031] The reaction steps and operation are the same as in Example 1, and the difference from Example 1 is that the copper salt is copper chloride. The reaction was stopped, and the target product 1a was obtained after post-treatment (yield 40%).

Embodiment 3

[0033] The reaction steps and operations are the same as in Example 1, except that the lithium salt is lithium chloride. The reaction was stopped, and the target product 1a was obtained after post-treatment (yield 10%).

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Abstract

The invention discloses a synthesis method of benzo[1,3]-tetrahydrothiazine derivatives. The method uses N,S-ketal derivatives with structural diversity as raw materials to synthesize benzo[1,3]-tetrahydrothiazine derivatives through an intramolecular cyclization reaction under the promotion of copper salts. Compared with the reported synthetic methods of benzo[1,3]-tetrahydrothiazine derivatives, the present invention has the advantages of low toxicity of reaction raw materials, simple operation, mild reaction conditions, high reaction efficiency and the like.

Description

technical field [0001] The invention relates to a synthesis method of benzo[1,3]-tetrahydrothiazine derivatives. Using N,S-ketene derivatives as raw materials, copper salts as accelerators, and lithium salts as additives, in organic solvents, under heating conditions, through intramolecular cyclization reactions to generate benzo[1,3]-tetra Hydrothiazide derivatives. [0002] Compared with the reported synthesis method of benzo[1,3]-tetrahydrothiazine derivatives, the present invention has low toxicity of reaction raw materials, simple operation, mild reaction conditions, high reaction efficiency, and the yield is 68%-76%. And the product has good functional group diversity. Background technique [0003] Benzo[1,3]-tetrahydrothiazine compound and its derivatives are important pharmaceutical intermediates, which are widely used in the fields of medicine, pesticide and chemical industry. Such compounds are analogs of psychotropic drugs such as phenothiazine, chlorophenothia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/08
CPCC07D279/08
Inventor 吴凯凯余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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