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Preparation method of naphtho[1,8-de][1,3]thiazin-2-mercaptan

A technology of thiazine and thiol, applied in the field of preparation of naphtho[1,8-de][1,3]thiazine-2-thiol, which can solve the problems of no mature synthetic route

Active Publication Date: 2020-06-16
NORTHWESTERN POLYTECHNICAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of the potential application value of naphthalene[1,8-de][1,3]thiazine-2-thiol and no mature synthetic route, we developed an efficient and practical synthetic naphthalene[1,8-de] A new approach to [1,3]thiazine-2-thiols

Method used

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  • Preparation method of naphtho[1,8-de][1,3]thiazin-2-mercaptan

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specific Embodiment approach

[0031] Using 1,8-dinaphthylamine as a starting material, react with sodium nitrite under acidic conditions, and then generate 8-halogenated-1-aminonaphthalene (1) under the action of copper powder. Under nitrogen protection afterwards, with (1) as reaction raw material, carbon disulfide is sulfur source, DBU (1,8-diazabicycloundec-7-ene) is base, copper (I) is catalyst, and reaction The solution is put into a reaction vessel together, reacted under heating conditions, concentrated and separated and purified to obtain naphthalene[1,8-de][1,3]thiazine-2-thiol.

[0032] The 8-halo-1-aminonaphthalene (1) is: 8-iodo-1-naphthylamine, 8-bromo-1-naphthylamine, 8-chloro-1-naphthylamine.

[0033] The copper (I) catalyst is a copper catalyst commonly used in laboratories such as cuprous iodide, cuprous bromide, cuprous oxide, cuprous chloride, cupric bromide, and cupric chloride.

[0034] The molar ratio of the 8-halogenated-1-aminonaphthalene (1) to carbon disulfide is (1~2): (2~6); th...

Embodiment 1

[0040] Embodiment 1: by 8-bromo-1-naphthylamine synthetic preparation method is implemented according to the following steps:

[0041] Using 1,8-dinaphthylamine (10g, 63mmol, 1 equivalent) as a raw material, using a mixed solution of acetic acid and water as a solvent (120mL acetic acid and 80mL water), react with sodium nitrite (4.4g, 69mmol, 1 equivalent) , then filtered to remove acetic acid, then added excess hydrobromic acid and copper powder (4.0g, 63mmol, 1 equivalent), reacted for 6 hours, neutralized the reaction solution, extracted, concentrated, and separated by column chromatography to obtain 8-bromo-1- Naphthylamine, off-white solid, yield 9.372g, 67%.

Embodiment 2

[0042] Embodiment 2: by the synthetic method of 8-iodo-1-naphthylamine, implement according to the following steps:

[0043] Using 1,8-dinaphthylamine (10g, 63mmol, 1 equivalent) as a raw material, using a mixed solution of acetic acid and water as a solvent (120mL acetic acid and 80mL water), react with sodium nitrite (4.4g, 69mmol, 1 equivalent) , then filtered to remove acetic acid, then added excess hydroiodic acid and copper powder (4.0g, 63mmol, 1 equivalent), reacted for 6 hours, neutralized the reaction solution, extracted, concentrated, and separated by column chromatography to obtain 8-bromo-1- Naphthylamine, off-white solid, yield 10.385 g, 61%.

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Abstract

The invention relates to a preparation method of naphtho[1,8-de][1,3]thiazin-2-mercaptan, and belongs to the field of organic synthesis. The preparation method comprises the steps that: 1,8-dinaphthylamine serves as a starting raw material and reacts with sodium nitrite under the acidic condition, and then 8-halogenated-1-aminonaphthalene (1) is generated under the action of copper powder; 8-halogenated-1-aminonaphthalene (1) serving as a reaction raw material and copper (I) salt serving as a catalyst react with carbon disulfide, concentration, separation and purification are carried out to obtain naphtho[1,8-de][1,3]thiazin-2-mercaptan. The method has the advantages that naphtho[1,8-de][1,3]thiazin-2-mercaptan can be obtained only through two-step reaction, and the method is mild in condition, simple to operate, high in yield and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of naphtho[1,8-de][1,3]thiazine-2-thiol. Background technique [0002] Thiazine is a class of heterocyclic compounds containing sulfur and nitrogen elements. Studies have shown that thiazide and its derivatives can be used in diuretics, anti-tumor drugs, anti-tuberculosis drugs, HIV inhibitors, insecticides, dyes, etc., and have a wide range of applications in the fields of biomedicine, pesticides, and optoelectronic materials. However, the current research on the synthesis method and process of thiazine compounds mainly focuses on the benzothiazine heterocycle. Related studies on naphthazides have not received widespread attention. There are only two synthetic routes of naphthalene[1,8-de][1,3]thiazine-2-thiol reported so far. The first synthetic route: In 1981, Luisa reported a method for synthesizing naphthalene[1,8-de][1,3]thiazine-2-thiol, usi...

Claims

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Application Information

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IPC IPC(8): C07D279/08
CPCC07D279/08
Inventor 张秋禹周凤涛刘邦杰
Owner NORTHWESTERN POLYTECHNICAL UNIV
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