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Synthesis method and application of novel fluorine-containing oxime ethers

A synthesis method and technology of fluorine-containing oxime ether are applied in the synthesis field of novel fluorine-containing oxime ether, can solve rare problems and the like, and achieve the effect of high yield

Active Publication Date: 2020-01-17
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the C–H alkylation of 1H-quinoxalin-2-ones is still rare

Method used

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  • Synthesis method and application of novel fluorine-containing oxime ethers
  • Synthesis method and application of novel fluorine-containing oxime ethers
  • Synthesis method and application of novel fluorine-containing oxime ethers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The synthesis of embodiment 1 fluoroxime ether I

[0053](1) Dissolve 3.0 mmol of raw material oxime 1 (structural formula as follows), 9.0 mmol of potassium carbonate in 15 mL of acetonitrile, stir for 3 hours at room temperature, then add pentafluoropyridine, stir for 12 hours at room temperature, and then spot the plate to confirm the completion of the reaction After that, the reaction solution is obtained;

[0054] (2) The reaction solution was spin-dried in vacuum, extracted 3 times with ethyl acetate and a saturated aqueous sodium chloride solution;

[0055] (3) Eluting with ethyl acetate and petroleum ether with a volume ratio of 2% yielded 596.8 mg of a yellow liquid with a yield of 85%. The product was tested by NMR, IR and mass spectrometry.

[0056] The NMR test results are as follows: 1 H NMR(400MHz,Chloroform-d)δ3.11(t,J=8.0Hz,2H),3.02(t,J=8.0Hz,2H),2.03–2.12(m,2H); 19 F NMR (376MHz, Chloroform-d) δ-90.51–90.34(m),-155.72–155.55(m); 13 C{ 1 H}NMR (100MH...

Embodiment 2

[0061] Embodiment 2 Synthesis of fluoroxime ether II-1

[0062] (1) Dissolve 3.0 mmol of raw material oxime 2 (structural formula as follows), 9.0 mmol of potassium carbonate in 15 mL of acetonitrile, stir and react for 3 hours at room temperature, then add pentafluoropyridine, stir and react for 12 hours at room temperature, and then spot the plate to confirm the completion of the reaction After that, the reaction solution is obtained;

[0063] (2) The reaction solution was spin-dried in vacuum, extracted 3 times with ethyl acetate and a saturated aqueous sodium chloride solution;

[0064] (3) Eluting with ethyl acetate and petroleum ether with a volume ratio of 2% yielded 842.5 mg of a white solid with a yield of 78%. The product was tested by NMR, IR and mass spectrometry.

[0065] NMR test results are: 1 H NMR (400MHz, Chloroform-d) δ7.80–7.86(m,3H),7.69(s,1H),7.45–7.52(m,2H),7.38–7.40(m,1H),3.83–3.91(m ,1H),3.68–3.61(m,1H),3.53–3.61(m,1H),3.27–3.38(m,2H); 19 F NMR (37...

Embodiment 3

[0070] Embodiment 3 Synthesis of fluoroxime ether II-2

[0071] (1) Dissolve 3.0 mmol of the raw material oxime 3 (structural formula is as follows), 9.0 mmol of potassium carbonate in 15 mL of acetonitrile, stir for 3 hours at room temperature, then add pentafluoropyridine, stir for 12 hours at room temperature, and then spot the plate to confirm the completion of the reaction After that, the reaction solution is obtained;

[0072] (2) The reaction solution was spin-dried in vacuum, extracted 3 times with ethyl acetate and a saturated aqueous sodium chloride solution;

[0073] (3) Eluting with ethyl acetate and petroleum ether with a volume ratio of 2%, 1435.5 mg of a white solid was obtained with a yield of 80%. The product was tested by NMR, IR and mass spectrometry.

[0074] NMR test results are: 1 H NMR (400MHz, Chloroform-d)δ5.02(s,1H),4.31(s,1H),3.56–3.62(m,1H),3.42–3.48(m,1H),3.05–3.15(m,2H ),1.47(s,9H); 19 F NMR (375MHz, Chloroform-d) δ-90.23–90.06(m),-155.57–157....

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Abstract

The invention discloses a synthesis method and application of novel fluorine-containing oxime ethers, belonging to the technical field of organic synthesis. The structural formula of the novel fluorine-containing oxime ether is one selected from the group consisting of formulas I to V. The formulas are as described in the specification. In the structural formulas, R is 2-Naphth or NHBoc, and Y isO or NBoc. Five fluorine-containing oxime ethers with new structures are provided in the invention, and due to the strong electron withdrawing capacity of -C5F4N, an N-O bond is particularly easy to crack uniformly under a heating or photocatalysis condition and can further participate in a free-radical relay reaction. A fluorine-containing oxime ether participated activated C-H bond free radicalreaction formed in the invention replaces traditional transition metal catalytic activation, and the reaction is a simple and environment-friendly manner for drug synthesis and natural product modification and has a high yield of up to 90%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method and application of a novel fluoroxime ether. Background technique [0002] 1H-quinoxalin-2-one is a kind of pharmaceutical compound with special structure. Due to the important biological properties of azoheterocyclic compounds, chemists have done a lot of research on their synthesis. In recent years, some important research progress has been reported, including free radical C 3 -Harylation, phosphorylation, amination and acylation of 1H-quinoxalin-2-ones. However, the C–H alkylation of 1H-quinoxalin-2-ones is still rare. Because of their importance, the introduction of alkyl substituents at the 3-position of 1H-quinoxalin-2-ones, especially those bearing functional groups, may facilitate their application in new drug discovery and development. On the other hand, cyanoalkyl compounds not only widely exist in various natural products an...

Claims

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Application Information

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IPC IPC(8): C07D213/68C07D401/12C07D405/12C07D241/44C07C253/00C07C255/35
CPCC07C253/00C07D213/68C07D241/44C07D401/12C07D405/12C07C255/35
Inventor 阳华向皞月夏鹏举胡远卓
Owner CENT SOUTH UNIV
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