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1,2,4-oxadiazine-5-ketone compounds and preparation method

A ketone compound and oxadiazine technology, which is applied in the fields of organic synthesis and medicine, can solve the problems of long reaction steps, long reaction time, complicated operation and the like, and achieves the effects of mild reaction conditions, novel reaction and simple operation.

Inactive Publication Date: 2017-07-18
CHENGDU LIKAI CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have certain limitations, such as narrow application range, long reaction time, long reaction steps, cumbersome operation, low product yield, large environmental pollution, etc.

Method used

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  • 1,2,4-oxadiazine-5-ketone compounds and preparation method
  • 1,2,4-oxadiazine-5-ketone compounds and preparation method
  • 1,2,4-oxadiazine-5-ketone compounds and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment one: synthetic compound 3a

[0029]

[0030] Add N-(benzyloxy)-2-bromo-2-methylpropionamide (1) (0.12mmol, 32.7mg), N-α-diphennitrone (2) (0.1 mmol, 19.7 mg), and 2 mL of solvent, then base (0.3 mmol) was added, and the reaction mixture was stirred at room temperature for the corresponding time (TLC monitoring). Separation and purification obtained white solid 3a, and the results of its partial reaction are shown in Table 1:

[0031] Table 1 Screening of reaction conditions for the synthesis of compound 3a

[0032]

[0033]

[0034] The hydrogen spectrum of the obtained compound 3a (such as figure 1 shown), carbon spectrum (such as figure 2 shown) and mass spectrometry (as image 3 Shown) The data is as follows:

[0035] 1 H NMR (300MHz, CDCl 3 )δ7.44–7.36(m,3H),7.36–7.23(m,7H),7.19(t,J=7.7Hz,2H),6.98(t,J=7.3Hz,1H),6.83(d,J =8.2Hz,2H),5.65(s,1H),5.18(d,J=10.0Hz,1H),4.65(d,J=10.0Hz,1H),1.75(s,3H),1.69(s,3H );

[0036] 13 C NMR (75MHz, CDCl...

Embodiment 2

[0038] Embodiment two: synthetic compound 3b

[0039]

[0040] Add N-(benzyloxy)-2-bromo-2-methylpropanamide (1) (0.12mmol), N-phenyl α-4-methylphenylnitrone (2 ) (0.1mmol), and 2mL HFIP, then triethylamine (0.3mmol) was added, and the reaction mixture was stirred at room temperature for 2h (monitored by TLC), separated and purified to obtain a white solid 3b with a yield of 97%.

[0041] The hydrogen spectrum, carbon spectrum and mass spectrum data of compound 3b obtained are as follows:

[0042] 1 H NMR (300MHz, CDCl 3 )δ7.43–7.28(m,5H),7.21–7.08(m,4H),7.05(d,J=8.0Hz,2H),6.94(t,J=7.4Hz,1H),6.80(d,J =7.8Hz,2H),5.59(s,1H),5.14(d,J=10.1Hz,1H),4.63(d,J=10.1Hz,1H),2.29(s,3H),1.71(s,3H ),1.65(s,3H); 13 C NMR (75MHz, CDCl3 )δ170.17, 145.53, 139.06, 134.81, 130.46, 129.89, 128.87, 128.75, 128.68, 128.54, 128.44, 123.47, 117.99, 83.47, 83.35, 77.23, 23.89, 21.41, 21. 25 h 26 N 2 NaO 3 [M+Na] + :425.1836; found: 425.1830.

Embodiment 3

[0043] Embodiment three: synthetic compound 3c

[0044]

[0045] Add N-(benzyloxy)-2-bromo-2-methylpropanamide (1) (4.5 mmol), N-phenyl α-4-bromophenylnitrone (2 ) (3.0mmol), and 2mL HFIP, then added triethylamine (9.0mmol), the reaction mixture was stirred at room temperature for 2h (monitored by TLC), separated and purified to obtain a white solid 3c with a yield of 97%.

[0046] The hydrogen spectrum, carbon spectrum and mass spectrum data of compound 3c obtained are as follows:

[0047] 1 H NMR (300MHz, CDCl 3 )δ7.55–7.21(m,7H),7.17(t,J=7.9Hz,2H),7.07–6.89(m,3H),6.75(d,J=7.8Hz,2H),5.52(s,1H ), 5.14(d, J=10.3Hz, 1H), 4.69(d, J=10.3Hz, 1H), 1.68(s, 3H), 1.64(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ 170.37, 145.17, 134.68, 132.43, 131.20, 130.26, 129.88, 129.01, 128.70, 128.54, 123.84, 123.41, 117.95, 83.58, 83.23, 77.30, 23.88, 23.36 for CCMS (HR.CalES); 24 h 23 BrN 2 NaO 3 [M+Na] + :489.0784; found: 489.0773.

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Abstract

The invention discloses 1,2,4-oxadiazine-5-ketone compounds and a preparation method, and relates to the field of organic synthesis and medicine. The 1,2,4-oxadiazine-5-ketone derivatives have a structure as shown in a structural formula (3). The preparation method of the 1,2,4-oxadiazine-5-ketone compounds comprises: respectively weighing an alpha-haloacetamides compound as shown in a formula (1) and a nitrone compound as shown in a formula (2); then adding a solvent; placing a mixture in a reaction container; stirring to react at a temperature of 0 DEG C to 50 DEG C; finally, adding alkali, continuously stirring, and after the reaction is completed, carrying out separation and purification to obtain the product. The invention discloses one type of novel 1,2,4-oxadiazine-5-ketone derivatives at first, and the compounds can be synthesized into a medicament with biological activity by simple structural modification. Moreover, the synthesis method has the advantages of reaction novelness, synthesis simplicity, simplicity for operation, mild reaction condition, high yield, atom economy and the like.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicine, in particular to 1,2,4-oxadiazin-5-one compounds and their preparation methods Background technique [0002] 1,2,4-Oxadiazin-5-ones are an important class of six-membered heterocyclic compounds containing nitrogen and oxygen atoms, which are widely used in the field of medicine. Studies have shown that these compounds have good biological activities, such as antibacterial, insecticidal, anti-inflammatory, anti-malarial, anti-tuberculosis and so on. Therefore, finding a simple and convenient method to synthesize 1,2,4-oxadiazin-5-one compounds can not only provide more new candidate molecules for the research and development of new drugs and drug screening, but also provide a basis for the synthesis of such drugs. Provide new methods. [0003] In addition, there are few methods for synthesizing 1,2,4-oxadiazin-5-ones, mainly including amino oxime and α-halogenated acid chloride (He...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D273/04A61P9/08A61P9/10
CPCC07D273/04
Inventor 袁伟成赵建强徐小英周晓建游勇王振华刘斌
Owner CHENGDU LIKAI CHIRAL TECH