Preparation method of 2-pyrrolyl-1,3-oxazacyclohexane compound

A technology for oxazines and compounds, which is applied in the field of organic chemical synthesis, can solve the problems of strong toxicity, difficult reaction connection of alkane long-chain structures, low product yield, etc., and achieves the effect of optimizing reaction conditions

Inactive Publication Date: 2018-11-02
HENAN UNIV OF SCI & TECH
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Problems solved by technology

[0005] The above route uses chiral amino acids as raw materials or substrates. According to the results of our previous preliminary experiments, we can successfully obtain the chiral target compound, but the product yield is not only low, but it is not difficult to see that the final ring-closing reaction condition is in benzene Backflow, strong toxicity and great harm; and compared with the compound Chinese Bittersweet Alkaloid (II), the obtained target product has a missing alkane long chain structure, which is difficult to be connected to the molecule through the reaction

Method used

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  • Preparation method of 2-pyrrolyl-1,3-oxazacyclohexane compound
  • Preparation method of 2-pyrrolyl-1,3-oxazacyclohexane compound
  • Preparation method of 2-pyrrolyl-1,3-oxazacyclohexane compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] (1) Knoevenagel condensation reaction

[0065] Add 0.1 mol of n-heptanal to the solvent dichloromethane, mix well; slowly add 0.1 mol of ethyl cyanoacetate and 0.25 g of sodium ethoxide solid catalyst under the condition of stirring at 20°C, then gradually raise the temperature to 35°C for reflux reaction for 4 hours, TLC tracking Reaction process; after the reaction, cool the reaction product to 20°C, filter to remove the precipitate, and obtain a mixture of 2-cyano-2-nonenoic acid-ethyl ester and unreacted raw materials; then add an equal volume of saturated salt to the mixture Water extraction, extraction twice, combined organic phases, dried to remove water, evaporated solvent to obtain 2-cyano-2-nonenoic acid-ethyl ester; yield 53%;

[0066] (2) Reduction reaction

[0067] The 2-cyano-2-nonenoic acid-ethyl ester prepared in step (1) and 0.4g lithium aluminum hydride were respectively dissolved in the solvent anhydrous ether to obtain 2-cyano-2-nonenoic acid-ethyl ...

Embodiment 2

[0071] (1) Knoevenagel condensation reaction

[0072] Add 0.2 mol of n-heptanal to the solvent dichloromethane, mix well; slowly add 0.2 mol of ethyl cyanoacetate and 0.35 g of sodium ethoxide solid catalyst under the condition of stirring at 25°C, then gradually raise the temperature to 40°C for reflux reaction for 4.5h, TLC Track the reaction process; after the reaction, cool the reaction product to 25°C, filter to remove the precipitate, and obtain a mixture of 2-cyano-2-nonenoic acid-ethyl ester and unreacted raw materials; then add an equal volume of saturated Extract with salt water, extract 3 times, take the organic phases and combine them, remove the water after drying, and evaporate the solvent to obtain 2-cyano-2-nonenoic acid-ethyl ester; the yield is 50%;

[0073] (2) Reduction reaction

[0074] The 2-cyano-2-nonenoic acid-ethyl ester prepared in step (1) and 0.5g lithium aluminum hydride were respectively dissolved in the solvent anhydrous ether to obtain 2-cyano...

Embodiment 3

[0078] (1) Knoevenagel condensation reaction

[0079] Add 0.3 mol of n-heptanal to the solvent dichloromethane, mix well; slowly add 0.3 mol of ethyl cyanoacetate and 0.45 g of sodium ethoxide solid catalyst under the condition of stirring at 30°C, then gradually raise the temperature to 50°C for reflux reaction for 5 hours, TLC tracking Reaction process; after the reaction, cool the reaction product to 30°C, filter to remove the precipitate, and obtain a mixture of 2-cyano-2-nonenoic acid-ethyl ester and unreacted raw materials; then add an equal volume of saturated salt to the mixture Extracted with water, extracted 3 times, combined the organic phases, dried to remove water, and evaporated the solvent to obtain 2-cyano-2-nonenoic acid-ethyl ester; the yield was 49%;

[0080] (2) Reduction reaction

[0081] The 2-cyano-2-nonenoic acid-ethyl ester prepared in step (1) and 0.6g lithium aluminum hydride were respectively dissolved in the solvent anhydrous ether to obtain 2-cya...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of a 2-pyrrolyl-1,3-oxazacyclohexane compound. The method comprises the following steps of mixing 2-pyrrolecarboxaldehyde and a solvent dichloromethane uniformly, adding a compound 1 and anhydrous magnesium sulfate under a stirring condition, reacting for 3-5 hours at 20-30DEG C, and removing impurities after reaction to obtain the 2-pyrrolyl-1,3-oxazacyclohexane compound. The invention provides a new synthetic strategy and method for a 2-pyrrolyl-1,3-oxazacyclohexane skeleton compound; the method lays a theoretical foundation for synthesis of NSCLC (non-small cell lung cancer)-resistant Chinese Bittersweet Alkaloid (II), which has an important application value, and other 1,3-oxazacyclohexane skeleton compound, and further provides a material and raw material guarantee for carrying out physiological and pharmacological activity research on 1,3-oxazacyclohexanealkaloid.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of 2-pyrrolyl-1,3-oxazepine compounds. Background technique [0002] The compound with 1,3-oxazidine skeleton, the previous research revealed that it has important highly selective inhibitory activity against non-small cell lung cancer (WP Yin, TZ Zhao, et al.Two alkaloids from Chinese bittersweetCelastrus angulatus.Phytochemistry , 1999, 52, 1731-1734.). It has been reported in the literature that 2-pyrrolyl-1,3-oxazacyclohexane (2-pyrrolyl-1,3-oxazcyclohexane) molecule is a class of molecules with a new skeleton extracted and isolated from the seed oil of the insecticidal plant Phyllostachys chinensis Alkaloid chiral compounds, among which Chinese BittersweetAlkaloid (II) exhibits good and highly selective inhibitory activity on non-small cell lung cancer. Due to the novel structure of the compound and its high selective inh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A61P35/00
CPCA61P35/00C07B2200/07C07D413/04
Inventor 尹卫平刘坤冯书晓赫红超
Owner HENAN UNIV OF SCI & TECH
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