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Preparation method of pyridino[1,2-a][1,3,5]-triazine-4-one compound

A technology of ketone compounds and pyridine, which is applied in the field of organic synthesis, can solve the problems of narrow substrate breadth, poor regioselectivity, and low reaction yield, and achieve the effect of convenient and easy-to-obtain raw materials, easy operation, and simple operation

Active Publication Date: 2018-04-06
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, most of the methods described above have some limitations, such as the need for pre-functionalization of substrates, the need for multi-step synthesis steps, poor regioselectivity, low reaction yields, narrow substrate breadth, etc.

Method used

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  • Preparation method of pyridino[1,2-a][1,3,5]-triazine-4-one compound
  • Preparation method of pyridino[1,2-a][1,3,5]-triazine-4-one compound
  • Preparation method of pyridino[1,2-a][1,3,5]-triazine-4-one compound

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Embodiment Construction

[0032] The present invention will be further described below in conjunction with specific embodiments.

[0033] Add potassium persulfate, potassium permanganate, imidazo[1,2-α]pyridine (II) and 2ml of organic solvent into a 35ml Schlenk tube according to the raw material ratio in Table 1, mix and stir evenly, and follow the reaction conditions in Table 2 After the reaction is completed, filter, mix the sample with silica gel, and obtain the corresponding pyrido[1,2-a][1,3,5]-triazin-4-one compound (I) through column chromatography purification, the reaction process is as follows: Shown:

[0034]

[0035] Table 1

[0036]

[0037]

[0038] Table 2

[0039]

[0040] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, CF 3 is trifluoromethyl, CN is cyano, Ph is phenyl.

[0041] The structural confirmation data of the compounds prepared in Examples 1-5:

[0042] The nuclear magnetic resonance of the pyrido[1,2-a][1,3,5]-triazin-4-one com...

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Abstract

The invention discloses a preparation method of a pyridino[1,2-a][1,3,5]-triazine-4-one compound, which includes the following steps: adding potassium persulfate, potassium permanganate, imidazole[1,2-alpha]pyridine and sodium azide into an organic solvent, heating the mixture to 120-140 DEG C to perform a reaction completely, and performing post-treatment to obtain the pyridino[1,2-a][1,3,5]-triazine-4-one compound. The preparation method has simple processes and employs easy-to-obtained raw materials, wherein the reaction is free of water-free and oxygen-free conditions and is free of heavymetals as catalysts. In addition, through proper design, different pyridino[1,2-a][1,3,5]-triazine-4-one compounds having different substituent group positions can be synthesized. The method is convenient to carry out and has excellent practicability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of pyrido[1,2-a][1,3,5]-triazin-4-one compound. Background technique [0002] [1,3,5]-Triazin-4-one compound, as an important nitrogen-containing fused heterocyclic ring, is widely used in the fields of organic synthesis, biology and pharmaceutical molecules (J.Med.Chem.1998,41,2985- 2993), many important molecular frameworks and synthetic precursors contain [1,3,5]-triazin-4-one structural units. For example, artificial carbodeoxynucleoside precursors, which can be efficiently converted into phosphoramidite reagents for DNA molecular synthesizers; in addition, [1,3,5]-triazin-4-one derivatives containing pyrazole rings can be as CRHR-1 / 5-HT 2 Antagonist; can also be used as an inhibitor of eosinophilia, etc.: [0003] [0004] There are three main methods for preparing pyrido[1,2-a][1,3,5]-triazin-4-one in current literature reports: one is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 陈铮凯曹刚剑任红军
Owner ZHEJIANG SCI-TECH UNIV