Synthesis method for iodoisoxazoline compound

A synthetic method and isoxazoline technology, which is applied in the field of synthesis of iodoisoxazoline compounds, can solve problems such as low utilization rate of atoms, expensive metal catalysts, and complicated operation conditions, and achieve low-cost, environment-friendly and low-cost reagents. Good material adaptability and high atom economy

Inactive Publication Date: 2019-02-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there have been some reports on the synthesis methods of this type of compounds, the synthesis methods reported in these documents have the disadvantages of using expensive metal catalysts, complicated operation conditions, and low atom utilization. Therefore, the development of novel and green chemical synthesis methods important to scientific research

Method used

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  • Synthesis method for iodoisoxazoline compound
  • Synthesis method for iodoisoxazoline compound
  • Synthesis method for iodoisoxazoline compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] 1-Phenylbut-3-en-1-one oxime (40.3, 0.25mmol), elemental iodine (31.8mg, 0.125mmol) and tert-butyl hydroperoxide (64.4mg, 0.5mmol, 70%wt aqueous solution) Join in the argon protection reaction bottle, add water 2ml again finally, react at room temperature 15h again, after the reaction finishes, use column chromatography (eluent: sherwood oil / ethyl acetate volume ratio 10:1) to separate Compound 1 (57.4 mg) was obtained with a yield of 80%.

[0033] Product characterization: white solid; m.p.72-73°C; 1 H NMR (500MHz, CDCl 3 )δ7.71–7.63(m,2H),7.48–7.38(m,3H),4.95–4.89(m,1H),3.52(dd,J=17.0,10.4Hz,1H),3.42(dd,J= 10.0,4.1Hz,1H),3.28–3.18(m,2H).

Embodiment 2

[0035]

[0036] 1-(4-Chlorophenyl)but-3-en-1-one oxime (48.9, 0.25mmol), elemental iodine (31.8mg, 0.125mmol) and tert-butyl hydroperoxide (64.4mg, 0.5mmol, 70%wt aqueous solution) joins in the argon protection reaction bottle, finally adds water 2ml again, reacts 15h at room temperature again, after reaction finishes, with column chromatography (eluent: sherwood oil / ethyl acetate volume ratio 10:1) Compound 2 (67.5 mg) was isolated with a yield of 84%.

[0037] Product characterization: white solid: m.p.98-99°C; 1 H NMR (500MHz, CDCl 3)δ7.65–7.55(m,2H),7.46–7.31(m,2H),4.96–4.90(m,1H),3.49(dd,J=17.0,10.4Hz,1H),3.42(dd,J= 10.1,4.0Hz,1H),3.29–3.10(m,2H).

Embodiment 3

[0039]

[0040] 1-(p-tolyl)but-3-en-1-one oxime (43.8, 0.25mmol), elemental iodine (31.8mg, 0.125mmol) and tert-butyl hydroperoxide (64.4mg, 0.5mmol, 70% wt aqueous solution) was added in the argon-protected reaction flask, and finally 2ml of water was added, and then reacted at room temperature for 15h. After the reaction, column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 10: 1) Compound 3 (48.2 mg) was isolated with a yield of 64%.

[0041] Product characterization: white solid; m.p.96–97°C; 1 H NMR (500MHz, CDCl 3 )δ7.61–7.50(m,2H),7.22(d,J=8.0Hz,2H),4.94–4.88(m,1H),3.50(dd,J=17.0,10.3Hz,1H),3.42(dd ,J=10.0,4.1Hz,1H),3.27–3.16(m,2H),2.38(s,3H).

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Abstract

The invention discloses a synthesis method for an iodoisoxazoline compound shown as formula (II). The method includes: dissolving ketoxime shown as formula (I), an iodine source and an oxidant mixedlyin a solvent, carrying out reaction for 7-15h at 25DEG C-60DEG C in the presence of an inert gas, and subjecting the obtained reaction liquid to post-treatment so as to obtain the isoxazoline compound shown as formula (II). The method provided by the invention directly takes ketoxime as the raw material for intramolecular cyclization reaction. The whole process has no need for a metal catalyst, avoids metal residue, and has high atom economy, also the reagents are cheap and environment-friendly, and the reaction operation is simple, therefore the method is more beneficial to application in pharmaceutical synthesis.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing iodoisoxazoline compounds. (2) Background technology [0002] Isoxazoline compounds are very important structural units that can be transformed into many other important organic compounds. [0003] Compounds such as the isoxazoline moiety contained in their molecules show impressive anti-inflammatory, antifungal and antibacterial activities. The compound can also be applied to synthesize a simple isoxazoline derivative, which is a very effective inhibitor of DNA methyltransferase. Although there have been some reports on the synthesis methods of this type of compounds, the synthesis methods reported in these documents have the disadvantages of using expensive metal catalysts, complicated operation conditions, and low atom utilization. Therefore, the development of novel and green chemical synthesis methods It is of great significance to scientific research. (3) Contents of the invention [000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/04C07D413/04C07D261/20
CPCC07D261/04C07D261/20C07D413/04
Inventor 李小青王鑫强许响生
Owner ZHEJIANG UNIV OF TECH
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