Synthetic method of naphtho [2, 1-d] oxazole compound

A synthesis method and technology of amine compounds, applied in the direction of organic chemistry, etc., can solve problems such as inhibiting application development

Pending Publication Date: 2022-08-09
HUNAN FIRST NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the complex raw material synthesis process also inhibits its application development

Method used

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  • Synthetic method of naphtho [2, 1-d] oxazole compound
  • Synthetic method of naphtho [2, 1-d] oxazole compound
  • Synthetic method of naphtho [2, 1-d] oxazole compound

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preparation example Construction

[0088] A method for synthesizing naphtho[2,1-d]oxazole compounds, characterized in that the preparation raw materials of the naphtho[2,1-d]oxazole compounds include: naphthol compounds, amine compounds Compound, 2,2,6,6-tetramethylpiperidine nitrogen oxide (TEMPO), oxidizing agent; comprising the following steps: at the beginning of the reaction, taking naphthol compound, amine compound, oxidizing agent, TEMPO, solvent and placing it in the reaction In a container, mix; under an inert gas atmosphere, heat and stir to react for a certain period of time, after the reaction is completed, it is cooled to room temperature, washed with saturated NaCl, then extracted with ethyl acetate, dried, concentrated under reduced pressure to remove the solvent, and the crude product is subjected to column chromatography. Separation to obtain the target product; the synthetic method of the naphtho[2,1-d]oxazole compounds has the following reaction formula:

[0089]

[0090] In the reaction f...

Synthetic example 1

[0110] Synthesis of 2-phenylnaphtho[2,1-d]oxazole

[0111] Take 2-naphthol, benzylamine, ammonium persulfate, TEMPO, and acetonitrile, put them in a reaction vessel, and mix them; under a nitrogen atmosphere, at a reaction temperature of 50 °C, the reaction is continued to stir for 8 hours. After the reaction, it was cooled to room temperature, washed with saturated NaCl, then extracted with ethyl acetate, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product in a yield of 70%. 1 H NMR (400MHz, CDCl 3 ): δ8.40–8.24(m,3H),7.96(d,J=8.2Hz,1H),7.85(d,J=8.7Hz,1H),7.78(d,J=8.7Hz,1H),7.64 (t, J=7.6Hz, 1H), 7.51–7.55 (m, 4H); 13 C NMR (101MHz, CDCl 3 ):δ162.4,146.4,138.6,131.7,131.1,128.9,128.7,127.4,127.3,126.8,125.6,125.4,120.4,120.2,118.6.

Synthetic example 2

[0113] Synthesis of 2-(2-methyl)phenylnaphtho[2,1-d]oxazole

[0114] 2-Naphthol, p-methylbenzylamine, ammonium persulfate, TEMPO, and acetonitrile were placed in a reaction vessel and mixed; under a nitrogen atmosphere, at a reaction temperature of 50°C, the reaction was continued to stir for 8h. After the reaction was completed, it was cooled to room temperature, washed with saturated NaCl, then extracted with ethyl acetate, dried, evaporated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 68%. 1 H NMR (400MHz, CDCl 3 ):δ8.28(t,J=8.5Hz,2H),7.96(d,J=8.2Hz,1H),7.89(d,J=8.7Hz,1H),7.78(d,J=8.7Hz,1H) ), 7.63(t, J=7.5Hz, 1H), 7.52(t, J=7.6Hz, 1H), 7.45–7.33(m, 3H), 2.89(s, 3H); 13 CNMR (101MHz, CDCl 3 ):δ162.7,145.9,138.4,138.3,131.7,131.5,130.5,129.6,128.6,126.7,126.3,126.0,125.5,125.1,120.2,120.2,118.7,22.3.HRMS(EI)m / z:[M] + calcd.for C 18 H 13 NO:259.0997; found:259.0996...

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Abstract

The invention provides a method for synthesizing a naphthol [2, 1-d] oxazole compound through oxidative cyclization of a naphthol compound and an amine compound under a metal-free condition. Many functional groups, such as Me, OMe, tBu, F, Cl, Br, I, CF3, CN, NO2, CHO, ester and anhydride groups, furfuryl, thienyl and pyridyl, are easily transferred into the desired product, which is not achieved by other methods. Based on the advantage, the method can provide a variety of new naphtho [2, 1-d] oxazole compounds. The method has the advantages of being high in universality, high in efficiency, good in selectivity, good in atom and step economy, easy in substrate obtaining, mild in condition, easy and convenient to operate and the like, and therefore the reaction can be widely applied to the fields of chemistry, biology, medicine and material science.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing naphtho[2,1-d]oxazole compounds. 【Background technique】 [0002] In 1906, Fisher first synthesized 2-methylnaphtho[2,1-d]oxazole; since then, scientists have conducted extensive research on the biological activity and photophysical properties of naphtho[2,1-d]oxazole derivatives, and used them as antibacterial agents, cysteine ​​protease inhibitors, anticancer agents, OLED materials, etc. In addition, many natural products also contain naphthooxazole skeletons, such as Salviamine B and Neosalvianen, etc. The traditional method of synthesizing naphtho[2,1-d]oxazole relies on the condensation and cyclization of 2-amino-1-naphthol and carboxylic acid derivatives, which are highly toxic. However, the preparation of 2-amino-1-naphthol raw materials requires a highly polluting nitration process and harsh reaction conditions, and it is difficult to extend th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/60C07D263/52
CPCC07D263/60C07D263/52
Inventor 董建玉武少峰莫敏
Owner HUNAN FIRST NORMAL UNIV
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