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A kind of preparation method of naphtho[1,8-de][1,3]thiazine-2-thiol

A technology of thiazine and thiol, which is applied in the field of preparation of naphtho[1,8-de][1,3]thiazine-2-thiol, can solve problems such as lack of mature synthesis routes, and achieve high safety Effect

Active Publication Date: 2022-07-26
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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specific Embodiment approach

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

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

[0033] The copper(I) catalysts are copper catalysts 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-...

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 (10 g, 63 mmol, 1 equiv) as raw material, using a mixed solution of acetic acid and water as solvent (120 mL acetic acid and 80 mL water), react with sodium nitrite (4.4 g, 69 mmol, 1 equiv) , 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 9.372 g, 67%.

Embodiment 2

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

[0043] Using 1,8-dinaphthylamine (10 g, 63 mmol, 1 equiv) as raw material, using a mixed solution of acetic acid and water as solvent (120 mL acetic acid and 80 mL water), react with sodium nitrite (4.4 g, 69 mmol, 1 equiv) , 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, 10.385 g, 61% yield.

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Abstract

The invention relates to a preparation method of naphtho[1,8-de][1,3]thiazine-2-thiol, belonging to the field of organic synthesis. The invention uses 1,8-dinaphthylamine as a starting material, Under acidic conditions, it reacts with sodium nitrite, and then generates 8-halogenated-1-aminonaphthalene (1) under the action of copper powder. Under nitrogen protection, 8-halogenated-1-aminonaphthalene (1) is used as the reaction raw material, and copper (I) salt is used as a catalyst to react with carbon disulfide, and through concentration, separation and purification, naphthalene [1,8-de] can be obtained. [1,3]thiazine-2-thiol. The advantage of this method is that naphthalene[1,8-de][1,3]thiazine-2-thiol can be obtained in only two steps, which has the advantages of mild conditions, simple operation and high yield.

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 thiazine and its derivatives can be used in diuretics, anti-tumor drugs, anti-tuberculosis drugs, HIV inhibitors, pesticides, dyes, etc., and have a wide range of applications in biomedicine, pesticides, optoelectronic materials and other fields. However, the current researches on the synthesis methods and processes of thiazine compounds mainly focus on benzothiazine heterocycles. The related research on naphthiazine compounds has not received extensive attention. There are only two synthetic routes for 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-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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