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Convenient Michaal addition reaction of 6-phenylimidazo[2, 1-b]thiazole

An addition reaction and phenyl technology, applied in the field of medicinal chemistry, to achieve the effect of mild conditions, efficient and convenient synthesis means, and convenient operation

Pending Publication Date: 2021-12-24
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the Michal addition reaction using imidazo[2,1-b]thiazole compounds as reaction raw materials and using cheap and easy-to-obtain Lewis acids as catalysts has not been reported.

Method used

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  • Convenient Michaal addition reaction of 6-phenylimidazo[2, 1-b]thiazole
  • Convenient Michaal addition reaction of 6-phenylimidazo[2, 1-b]thiazole
  • Convenient Michaal addition reaction of 6-phenylimidazo[2, 1-b]thiazole

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Experimental program
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Effect test

Embodiment 1

[0021] In a 25 mL test tube, add 0.2 mmol of 6-phenyl-imidazol[2,1-b]thiazole, 0.26 mmol of 1-penten-3-one, 0.4 mmol of acidic aluminum oxide, and 3 ml of n-hexane As a solvent, stir at 68 °C. After TLC (thin layer chromatography) detection, the reaction solution was cooled to room temperature, the reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product with a yield of 76%.

[0022] The structural characterization data of the resulting product are as follows:

[0023] 1 H NMR (500MHz, CDCl 3 )δ7.69(d, J=6.8Hz, 2H), 7.52(d, J=4.5Hz, 1H), 7.42(t, J=7.7Hz, 2H), 7.30(t, J=7.6Hz, 1H) ,6.80(d,J=4.6Hz,1H),3.28(t,J=7.0Hz,2H),2.79(t,J=7.1Hz,2H),2.38(q,J=7.3Hz,2H),1.02 (t,J=7.3Hz,3H);

[0024] 13 C{ 1 H}NMR (125MHz, CDCl 3 )δ210.2, 147.9, 143.1, 134.9, 128.6, 127.1, 127.0, 121.4, 117.8, 112.1, 41.1, 36.1, 18.8, 7.7.

[0025] According to the abo...

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Abstract

The invention relates to a convenient Michaal addition reaction of 6-phenylimidazo[2, 1-b]thiazole. The method comprises the following steps: adding 6-phenylimidazo[2, 1-b]thiazole, 1-pentene-3-one, Lewis acid and a solvent into a reaction container, stirring and reacting at 40-150 DEG C for 1-10 hours, cooling to room temperature after the reaction is finished, filtering the obtained reaction liquid, evaporating the solvent under reduced pressure to obtain a crude product, and purifying by column chromatography to obtain the Michal addition product. The convenient Michael addition reaction of 6-phenylimidazo[2, 1-b]thiazole has the characteristics of convenient operation, mild conditions, easily available raw materials, good functional group tolerance and the like, and has important research value on the Michael addition reaction of sulfur-containing heterocycles such as imidazo[2, 1-b]thiazole.

Description

technical field [0001] The invention relates to the technical fields of medicinal chemistry, life science, organic synthesis, etc., and in particular relates to a convenient Michal addition reaction of 6-phenyl-imidazol[2,1-b]thiazole. Background technique [0002] Imidazol[2,1-b]thiazole compounds occupy an important research position in the fields of medicinal chemistry and life science because of their unique heterocyclic structure. Many drug molecules and drug molecule precursors contain this core structure. Therefore, the research on the functional group reaction of imidazo[2,1-b]thiazole compounds has always been a research hotspot in the field of organic synthesis. At present, there has been no relevant report on the Michal addition reaction using imidazo[2,1-b]thiazole compounds as reaction raw materials and using cheap and easily available Lewis acids as catalysts. This method provides a simple and feasible synthetic route for the construction of alkyl-substituted...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 及方华王守才李璇
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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