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Synthesis method of 1, 3-diaryl substituted tetrazolone inner salt

A synthesis method and technology of tetrazolone, applied in the field of organic chemical synthesis, can solve the problems of low yield and the like, and achieve the effects of high yield, few by-products and convenient operation

Active Publication Date: 2021-03-30
JIANGXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Tetrazolone compounds can be prepared from acid chloride and trimethylsilyl azide at high temperature (Org.Biomol.Chem.2016,14,9338-9342), but this method is usually only used to synthesize monosubstituted tetrazolone
In the reported synthetic routes, a variety of complex reaction raw materials and multi-step reactions are usually involved, and the yields are low

Method used

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  • Synthesis method of 1, 3-diaryl substituted tetrazolone inner salt
  • Synthesis method of 1, 3-diaryl substituted tetrazolone inner salt
  • Synthesis method of 1, 3-diaryl substituted tetrazolone inner salt

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preparation example Construction

[0030] The synthetic method comprises the following steps:

[0031] a. In the air atmosphere, after mixing 0.5mmol of diaryl semicarbazide with 10mol% catalyst palladium acetate, and adding 1.0mmol of potassium carbonate as alkali, the above mixed solution is placed in a solvent, and the reaction temperature is controlled at 70- Stir by magnetic force for 2-4 hours at 100°C;

[0032] b. During the reaction process, use TLC to monitor until the reaction is complete. After the reaction, cool down to room temperature. After the reaction, add an appropriate amount of water to quench the reaction, then add an appropriate amount of dichloromethane for extraction, dry over anhydrous sodium sulfate, and spin dry under reduced pressure The pure 1,3-diaryl substituted tetrazolone internal salt was separated by column chromatography.

[0033] In this embodiment, it is any one of dimethyl sulfoxide, tetrahydrofuran, and dioxane. The solvent is preferably dimethylsulfoxide.

[0034] In ...

Embodiment 1

[0040]

[0041] In air atmosphere, 0.5 mmol of diaryl semicarbazide, 10 mol% of palladium acetate, and 1.0 mmol of potassium carbonate were magnetically stirred in DMSO at 90° C. for 3 h, and the reaction was monitored by TLC until complete reaction. Add an appropriate amount of water to quench the reaction in the post-treatment, then add an appropriate amount of dichloromethane to extract, dry over anhydrous sodium sulfate, spin the solvent under reduced pressure, and then separate the pure 1,3-diphenyltetrazolone internal salt 2a by column chromatography . Isolated yield: 84%. The structure of the compound has been determined by single crystal X-ray diffraction, CCDC number: 1919662.

[0042] 1 H NMR (400MHz, CDCl 3 )δ8.17-8.11 (m, 4H), 7.59 (dd, J = 6.8, 4.0Hz, 3H), 7.55 (t, J = 7.8Hz, 2H), 7.45 (t, J = 7.4Hz, 1H); 13 C NMR (101MHz, CDCl 3 )δ159.45, 136.58, 134.28, 131.42, 129.80, 129.53, 128.71, 120.52, 119.98; HRMS (ESI-TOF) calcd.For C 13 h 10 N 4 NaO + :261....

Embodiment 2

[0044] In an air atmosphere, 0.5 mmol of diaryl semicarbazide, 10 mol% of palladium acetate, and 1.0 mmol of potassium carbonate were magnetically stirred in tetrahydrofuran at 80° C. for 3 h, and the reaction was monitored by TLC until complete reaction. Add an appropriate amount of water to quench the reaction in the post-treatment, then add an appropriate amount of dichloromethane to extract, dry over anhydrous sodium sulfate, spin the solvent under reduced pressure, and then separate the pure 1,3-diphenyltetrazolone internal salt 2a by column chromatography . Isolated yield: 58%.

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Abstract

The invention provides a method for synthesizing 1, 3-diaryl substituted tetrazolone inner salt, which comprises the following steps of: a, reacting a diaryl semicarbazide reagent serving as a reaction raw material in a reaction solvent under the action of a catalyst and alkali to obtain the 1, 3-diaryl substituted tetrazolone inner salt, mixing 0.5 mmol of diarylaminourea with 10 mol% of palladium acetate serving as a catalyst, adding 1.0 mmol of potassium carbonate serving as alkali, putting the mixed solution into a solvent, controlling the reaction temperature to be 70-100 DEG C, and magnetically stirring for 2-4 hours; b, in the reaction process, TLC is used for monitoring the complete reaction, after the reaction is finished, the temperature is reduced to the room temperature, afterthe reaction is finished, a proper amount of water is added for quenching reaction treatment, then a proper amount of dichloromethane is added for extraction, anhydrous sodium sulfate is added for drying, the solvent is subjected to reduced-pressure spin-drying, and then pure 1, 3-diaryl substituted tetrazolone inner salt is obtained through column chromatography separation.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for one-step synthesis of 1,3-diaryl substituted tetrazolone inner salt by palladium catalysis. Background technique [0002] As a nonclassical bioisostere of carboxylic acid, the tetrazole skeleton widely exists in drug molecules. For example, tetrapyrrole is an insecticide from the o-formamidobenzamide group. Oxygenated tetrazol-5-one (tetrazolone) at the 5-position of the tetrazole ring exists in the already marketed analgesic alfentanil molecule (J.Med.Chem.1986,29,11,2290 –2297). In addition, tetrazolone is also the core skeleton of a series of β3-adrenoceptor agonists (Bioorg. Med. Chem. Lett. 1999, 9, 1251-1254). [0003] Tetrazolone compounds can be prepared from acid chloride and trimethylsilyl azide at high temperature (Org. Biomol. Chem. 2016, 14, 9338-9342), but this method is usually only used to synthesize monosubstituted tetrazolone. In tetraz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 刘晋彪蔡颖叶秋香
Owner JIANGXI UNIV OF SCI & TECH
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