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Synthesis method of 1,3-oxazine hydroxylate

A synthetic method and technology of hydroxylation, applied in the direction of organic chemistry, etc., to achieve the effect of good practical value

Active Publication Date: 2020-08-28
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis method of 1,3-oxazine compounds is prepared by condensation of amino alcohols and carbonyl compounds (Chem. Eur J, 2008, 14, 3653), which limits the preparation of hydroxyl-containing 1,3-oxazine compounds

Method used

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  • Synthesis method of 1,3-oxazine hydroxylate
  • Synthesis method of 1,3-oxazine hydroxylate
  • Synthesis method of 1,3-oxazine hydroxylate

Examples

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Embodiment 1

[0021] A kind of synthetic method of 1,3-oxazine hydroxyl compound, comprises the following steps: 1) take p-toluimide homoallyl ester as substrate, silver acetate as carboxyl reagent, copper acetate as copper salt, Acetonitrile is the reaction solvent; 2) p-toluimide homoallyl ester (37.8mg, 0.2mmol), silver acetate (66.8mg, 0.4mmol), copper acetate (7.2mg, 0.04mmol) are added to Stirred 1,2-dichloroethane (2mL), reacted at 80°C for 24 hours, then obtained a colorless liquid (37.1mg, 75%) after extraction, drying, concentration and silica gel column chromatography, chemical reaction Formula 1 is:

[0022]

[0023] The product detection data are as follows:

[0024] 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=8.1Hz, 2H), 7.16(d, J=8.0Hz, 2H), 4.47–4.40(m, 1H), 4.34–4.25(m, 2H), 4.16–4.08(m ,1H),3.85–3.76(m,1H),2.36(s,3H),2.10(s,3H),2.09–2.02(m,1H),1.85–1.72(m,1H); 13 C NMR (101MHz, CDCl 3 ) δ 171.2, 156.2, 140.8, 131.1, 128.9, 127.2, 68.1, 64.0, 50.7, 24.9, 21.6, 21.2.

Embodiment 2

[0026] A kind of synthetic method of 1,3-oxazine hydroxyl compound, comprises the following steps: 1) take p-toluimide homoallyl ester as substrate, silver benzoate as carboxyl reagent, copper acetate as copper salt , acetonitrile is the reaction solvent; 2) p-toluimide homoallyl ester (37.8mg, 0.2mmol), silver benzoate (91.5mg, 0.4mmol), copper acetate (7.2mg, 0.04mmol) are followed by Added into stirred 1,2-dichloroethane (2mL), reacted at 80°C for 24 hours, then obtained a colorless liquid (50.2mg, 81%) after extraction, drying, concentration and silica gel column chromatography, Chemical reaction formula 2 is:

[0027]

[0028] The product detection data are as follows:

[0029] 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=8.1Hz, 2H), 7.16(d, J=8.0Hz, 2H), 4.47–4.40(m, 1H), 4.34–4.25(m, 2H), 4.16–4.08(m ,1H),3.85–3.76(m,1H),2.36(s,3H),2.10(s,3H),2.09–2.02(m,1H),1.85–1.72(m,1H); 13 C NMR (101MHz, CDCl 3 ) δ 166.6, 156.4, 140.9, 133.1, 131.0, 130.3, 129.8, 128.9, 128.5, 127....

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Abstract

The invention relates to a synthesis method of 1,3-oxazine hydroxylate, which comprises the following steps: 1) sequentially adding arylformamide homoallyl ester, silver carboxylate and copper salt into an organic solvent; and 2) heating to a proper temperature to obtain the carboxyl-containing 1,3-oxazine compound. According to the preparation method, aryl formamide homoallyl ester, silver carboxylate and copper salt are creatively used for preparing the novel hydroxyl-containing 1, 3-oxazine compound. Therefore, the method has good practical value, and has important reference significance for developing important bioactive molecules of 1, 3-oxazine.

Description

technical field [0001] The invention relates to a method for synthesizing 1,3-oxazine hydroxyl compounds, belonging to the technical field of organic synthesis. Background technique [0002] 1,3-oxazine is an important class of biologically active molecules, such as some β-amyloid precursor protein lyase inhibitors contain 1,3-oxazine structure. In the design and synthesis of innovative small molecule drugs, it is very easy to obtain small organic molecules with potential biological activity by derivatizing the active backbone. Since hydroxyl is a functional group that is easily derivatized and transformed, the introduction of hydroxyl or its derivatives into 1,3-oxazine bioactive molecules is helpful for further research on the biological activity of related compounds. At present, the synthesis method of 1,3-oxazine compounds is prepared by condensation of amino alcohols and carbonyl compounds (Chem. Eur J, 2008, 14, 3653), which limits the preparation of hydroxyl-containi...

Claims

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Application Information

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IPC IPC(8): C07D265/08
CPCC07D265/08
Inventor 牟学清陈永正李菲
Owner ZUNYI MEDICAL UNIVERSITY
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