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Synthetic method for spiro-cycle isoxazoline compound

A technology of spirocyclic isoxazoline and synthesis method, which is applied in the synthesis field of preparing spirocyclic isoxazoline compounds, can solve the problems of heavy metal environmental pollution, application restriction and the like, and achieves stable performance, high yield and wide sources. Effect

Inactive Publication Date: 2018-03-09
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this method, the use of heavy metals will cause serious pollution to the environment, which restricts the application of this method.

Method used

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  • Synthetic method for spiro-cycle isoxazoline compound
  • Synthetic method for spiro-cycle isoxazoline compound
  • Synthetic method for spiro-cycle isoxazoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1a (0.05 mmol, 10.1 mg), substrate 2a (0.25 mmol, 38.8 mg), triethylamine (0.25 mmol, 25.3 mg), DABCO (0.01 mmol, 1.12 mg) were successively weighed into the reaction tube, and the Nitrogen, and chloroform (0.15 mL) was added under nitrogen atmosphere, and reacted at 50° C. for 48 hours. After the reaction was detected by TLC, silica gel was directly added, and column chromatography was spin-dried to obtain a white solid 3aa (73%). 1 H NMR (CDCl 3, 500 MHz): δ(ppm) 7.73-7.72 (m, 2H), 7.51-7.39 (m, 6H), 7.36-7.26 (m,7H), 4.29-4.16 (m, 2H), 3.99 (δ, J = 20.0 Hz, 1H), 3.65 (δ, J = 20.0 Hz, 1H),3.37 (δ, J = 15.0 Hz, 1H), 2.99 (δ, J = 15.0 Hz, 1H), 1.17 (t, J = 10.0 Hz,3H). 13 C NMR (CDCl 3 , 125 mHz): Δ (PP) 166.8, 157.1, 156.6, 133.5, 130.9,130.5, 130.5, 129.1, 129.0, 128.2, 127.5, 126.9, 93.5, 62.1, 38.3, 14.0. HRMSSS (ESI): exact mass calculateδ for M + (C 27 h ...

Embodiment 2

[0017]

[0018] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1a (0.05 mmol, 10.1 mg), substrate 2b (0.25 mmol, 38.8 mg), triethylamine (0.25 mmol, 25.3 mg), DABCO (0.01 mmol, 1.12 mg) were successively weighed into the reaction tube, and the Nitrogen, and chloroform (0.15 mL) was added under nitrogen atmosphere, and reacted at 50°C for 48 hours. After the reaction was detected by TCL, directly add silica gel, spin dry column chromatography, and obtain white solid 3ab (87%). 1 HNMR (CDCl 3, 500 MHz): δ (ppm) 7.73-7.71 (m, 2H), 7.40-7.38 (m, 2H), 7.30-7.26(m,5H), 7.17-7.14 (m, 2H), 7.05-7.02 (m, 2H), 4.27-4.18 (m, 2H), 3.98 (δ, J =15.0 Hz, 1H), 3.57 (δ, J = 15.0 Hz, 1H), 3.37 (δ, J = 15.0 Hz, 1H), 2.98 (δ, J = 15.0 Hz, 1H), 1.17 (t, J = 10.0 Hz, 3H). 13 C NMR (CDCl 3 , 125 MHz): δ (ppm)166.8, 164.3 ( J = 1005.0 Hz), 164.1 ( J = 1005.0 Hz), 156.2, 155.6, 133.3,130.5, 129.1 ( J = 30.0 Hz), 129.0 ( J = 35.0 Hz), 128.4, 1...

Embodiment 3

[0020]

[0021] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. Substrate 1a (0.05 mmol, 10.1 mg), substrate 2c (0.25 mmol, 38.8 mg), triethylamine (0.25 mmol, 25.3 mg), DABCO (0.01 mmol, 1.12 mg) were successively weighed into the reaction tube, and the Nitrogen, and chloroform (0.15 mL) was added under nitrogen atmosphere, and reacted at 50°C for 48 hours. After the reaction was detected by TCL, silica gel was directly added, and column chromatography was spin-dried to obtain a white solid 3ac (58%). 1 HNMR (CDCl 3, 500 MHz): δ (ppm) 7.62-7.57 (m, 4H), 7.49-7.47 (m, 2H), 7.29-7.26(m, 5H), 7.25-7.23 (m, 2H), 4.28-4.17 (m, 2H), 3.97 (δ, J = 20.0 Hz, 1H),3.54 (δ, J= 20.0 Hz, 1H), 3.36 (δ, J = 15.0 Hz, 1H), 2.98 (δ, J = 15.0 Hz,1H), 1.17 (t, J = 10.0 Hz, 3H). 13 C NMR (CDCl 3 , 125 mHz): Δ (PP) 166.7,156.2, 155.8, 133.2, 132.4, 132.3, 130.5, 128.5, 128.3, 127.6, 126.9,125.8, 125.2, 99.7, 62.7, 38.0, 14.0, 14.0, 14.0 . HRMS (ESI): exactmas...

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Abstract

The invention discloses a synthetic method for a spiro-cycle isoxazoline compound. The method comprises the following steps: in a reaction solvent, using allenoate and chlorinated aldehyde oxime as reaction raw materials, using Lewis base as a catalyst, and reacting to obtain the spiro-cycle isoxazoline compound. The method has the characteristics of mild reaction condition, easy acquirement and favorable prices of the raw materials, simple reaction operation and higher productive rate, is capable of providing a key skeleton structure for the synthesis of a number of natural products and medicines, and can be extensively applied to the industrial-scale production.

Description

technical field [0001] The invention specifically relates to a synthetic method for preparing spirocyclic isoxazoline compounds, which belongs to the technical field of organic compound technology application. Background technique [0002] Spirocyclic isoxazoline compounds are a very important class of pharmaceutical and chemical intermediates with very high application value. There are isoxazoline skeletons in many drugs and bioactive molecules. At present, the traditional methods of synthesizing isoxazoline compounds are mainly prepared by metal-catalyzed methods. However, in this method, the use of heavy metals will cause serious pollution to the environment, which restricts the application of this method. In addition, spirocyclic isoxazoline compounds are rare in synthesis, and they are of great value in the field of biomedicine. Contents of the invention [0003] The present invention overcomes the above defects of the prior art, and innovatively proposes a green, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10
CPCC07D498/10
Inventor 李文军石振艳
Owner QINGDAO UNIV
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