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A kind of preparation method of gamma-butyrolactone and isoxazoline bicyclic skeleton compound

A skeleton compound and isoxazoline technology, applied in the field of heterocyclic compound synthesis, can solve the problems of narrow application range, harsh reaction conditions, complicated preparation of raw materials, etc. Effect

Active Publication Date: 2021-10-08
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, most of the currently reported methods for synthesizing γ-butyrolactone and isoxazoline bicyclic skeletons have the following disadvantages: complex preparation of raw materials, cumbersome reaction process, relatively harsh reaction conditions, narrow scope of application, relatively low yield Low

Method used

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  • A kind of preparation method of gamma-butyrolactone and isoxazoline bicyclic skeleton compound
  • A kind of preparation method of gamma-butyrolactone and isoxazoline bicyclic skeleton compound
  • A kind of preparation method of gamma-butyrolactone and isoxazoline bicyclic skeleton compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add compound 1a (10mmol, 2.02g), solvent-dried N,N-dimethylformamide (30mL), compound 2 (30mmol, 3.09g) to the reaction flask in sequence; then react in air at 25°C 20 hours; after the reaction was finished, it was quenched with saturated sodium chloride solution, and then extracted with ethyl acetate, the solvent was removed by a rotary evaporator, adsorbed on silica gel, and finally column chromatography was carried out with a mixed solvent of ethyl acetate and sherwood oil. Product 3a was obtained in 81% yield. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0033] 1 H NMR (400MHz, CDCl 3 )δ7.54–7.32(m,5H),5.76(d,J=12.5Hz,1H),4.76(t,J=8.6Hz,1H),4.45(t,J=8.6Hz,1H),4.37( dt,J=12.5,8.6Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ158.1, 157.2, 134.7, 129.7, 129.1, 126.8, 94.3, 69.9, 54.4; HRMS (ESI-TOF): AnalCalcd.For.C 11 h 9 NNaO 3 +...

Embodiment 2

[0035]

[0036] Add compound 1b (10mmol, 2.20g), solvent-dried N,N-dimethylformamide (30mL), and compound 2 (30mmol, 3.09g) to the reaction test tube in turn; then react in air at 25°C 16 hours; after the reaction was finished, it was quenched with saturated sodium chloride solution, and after extraction with ethyl acetate, the solvent was removed by a rotary evaporator, adsorbed on silica gel, and finally column chromatography was carried out with a mixed solvent of ethyl acetate and sherwood oil. Product 3b was obtained in 84% yield. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0037] 1 H NMR (400MHz, CDCl 3 )δ7.52–7.34(m,2H),7.22–7.01(m,2H),5.76(d,J=12.6Hz,1H),4.77(t,J=8.8Hz,1H),4.46(t,J =8.8Hz,1H),4.36(dt,J=12.6,8.8Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ163.3(d, J=249.4Hz), 158.1, 157.3, 130.5(d, J=3.3Hz), 128.9(d, J=8.6Hz), 116.2(d, J=21.9H...

Embodiment 3

[0039]

[0040] Add compound 1c (0.2mmol, 47.3mg), solvent-dried N,N-dimethylformamide (2mL), compound 2 (0.6mmol, 73μL) to the reaction tube in turn; React for 12 hours; after the reaction, quench with saturated sodium chloride solution, then extract with ethyl acetate, use a rotary evaporator to remove the solvent, adsorb on silica gel, and finally perform column chromatography with a mixed solvent of ethyl acetate and petroleum ether The product 3c was obtained with a yield of 89%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0041] 1 H NMR (400MHz, CDCl 3 )δ7.54–7.29(m, 4H), 5.74(d, J=12.6Hz, 1H), 4.77(t, J=8.8Hz, 1H), 4.45(t, J=8.8Hz, 1H), 4.34( dt,J=12.6,8.8Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ157.9, 157.3, 135.6, 133.3, 129.3, 128.2, 93.4, 69.8, 54.5; HRMS (ESI-TOF): AnalCalcd.For.C 11 h 8 ClNNaO 3 + +MeOH:292.0347,Found:292.0359;IR...

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Abstract

The invention relates to a preparation method of a γ-butyrolactone and isoxazoline bicyclic skeleton compound. The diazo compound and the nitrous acid lipid compound are reacted in an organic solvent at 25-80°C, and the γ- Butyrolactone and oxazoline bicyclic skeleton compound. The preparation method of the invention has the advantages of abundant raw material sources, wide applicability of reaction substrates, simple and convenient operation, and the like.

Description

technical field [0001] The invention relates to the technical field of synthesis of heterocyclic compounds, in particular to a preparation method of a γ-butyrolactone and isoxazoline bicyclic skeleton compound. Background technique [0002] As we all know, γ-butyrolactone and isoxazoline, as two important structural units of heterocyclic compounds, widely exist in drug molecules, materials and natural products. Although there are many methods for preparing these two skeletons, the construction of the γ-butyrolactone and isoxazoline bicyclic skeleton is still very imperfect. The γ-butyrolactone and isoxazoline bicyclic skeleton that takes into account these two structural units undoubtedly has a good application prospect in medicine, materials and metal complexes. Therefore, the rapid preparation of γ-butyrolactone and isoxazoline bicyclic skeleton has high practical value. [0003] Through investigation, it is found that the current methods for synthesizing γ-butyrolactone...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04C07D498/06
CPCC07D498/04C07D498/06
Inventor 万小兵马亮江港钟陶苏艳成雄略
Owner SUZHOU UNIV