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N,N-diamide substituted hydrazone derivative and synthesis method

A technology of diamide group and synthesis method, applied in the field of N,N-diamide group substituted hydrazone derivatives and synthesis, can solve problems such as lack of efficient synthesis, achieve good industrial application prospects, mild reaction conditions, no water and air sensitive effect

Active Publication Date: 2016-12-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the substrates of the above reactions and methods only involve N,N-dialkyl substituted hydrazone derivatives, while for other types of N,N-disubstituted hydrazone derivatives, such as N,N-diamide substituted hydrazone derivatives No relevant studies have been performed, which may be due to the lack of efficient methods for the synthesis of N,N-diamide-substituted hydrazone derivatives
However, there is no report on the direct and efficient synthesis of N,N-diamido-substituted hydrazone derivatives using N-p-toluenesulfonyl hydrazone as a raw material.

Method used

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  • N,N-diamide substituted hydrazone derivative and synthesis method
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  • N,N-diamide substituted hydrazone derivative and synthesis method

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Effect test

Embodiment 1

[0026] In a 25 ml reaction flask equipped with a reflux condenser, add 0.2 mmol of benzaldehyde-p-toluenesulfonyl hydrazone, 0.2 mmol of cesium carbonate, 0.01 mmol of palladium trifluoroacetate, 0.1 mmol of azodimethylformamide, 2 ml of toluene, the reaction system was stirred at 90° C. for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature. The reaction solution was extracted with ethyl acetate, the solvent was removed by rotary evaporation under reduced pressure, and the target product was obtained by separation and purification by column chromatography. The column chromatography eluent used was petroleum ether with a volume ratio of 2:1: ethyl acetate mixed solvent , the product was an oily liquid with a yield of 91%.

Embodiment 2

[0028] In a 25 ml reaction flask equipped with a reflux condenser, add 0.2 mmol of benzaldehyde-p-toluenesulfonyl hydrazone, 0.3 mmol of potassium carbonate, 0.01 mmol of palladium trifluoroacetate, 0.1 mmol of azodimethylformamide, 2 ml of toluene, the reaction system was stirred at 90° C. for 12 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature. The reaction solution was extracted with ethyl acetate, the solvent was removed by rotary evaporation under reduced pressure, and the target product was obtained by separation and purification by column chromatography. The column chromatography eluent used was petroleum ether with a volume ratio of 2:1: ethyl acetate mixed solvent , the product was an oily liquid with a yield of 83%.

Embodiment 3

[0030] In a 25 ml reaction flask equipped with a reflux condenser, add 0.2 mmol of benzaldehyde-p-toluenesulfonyl hydrazone, 0.2 mmol of potassium tert-butoxide, 0.01 mmol of palladium trifluoroacetate, 0.1 mmol of azodimethylformamide , 2 ml of toluene, the reaction system was stirred at 90 ° C for 12 hours, the heating and stirring were stopped, and it was cooled to room temperature. The reaction solution was extracted with ethyl acetate, the solvent was removed by rotary evaporation under reduced pressure, and the target product was obtained by separation and purification by column chromatography. The column chromatography eluent used was petroleum ether with a volume ratio of 2:1: ethyl acetate mixed solvent , the product was an oily liquid with a yield of 86%.

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Abstract

The invention belongs to the technical field of medical and chemical synthesis, and discloses a N,N-diamide substituted hydrazone derivative and a synthesis method. The synthesis method method includes the following steps that in a reactor, N-p-tosyl hydrazone, azo dialkyl diamide, alkali, a palladium salt catalyst and solvent are added and react for 12-24 h in a stirred mode at the temperature of 70-90 DEG C, after reaction is completed, the mixture is cooled to room temperature, ethyl acetate is used for extracting reaction liquor, the solvent is evaporated in a pressure reduction mode to obtain a crude product, and the N,N-diamide substituted hydrazone derivative is obtained through column chromatography purification. Palladium salt low in price and easy to obtain is used, and the raw materials are nontoxic, low in cost and easy to obtain; reaction is high in adaptability to a functional group and substrates, the product yield is high, the product can be produced and synthesized on a gram-level scale, which is beneficial for industrial production, and the obtained product has wide application in pesticide, medicine and material fields.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to an N,N-diamido-substituted hydrazone derivative and a synthesis method. Background technique [0002] N,N-disubstituted hydrazone derivatives are a very important class of synthetic intermediates, ligands and catalysts (Job, A.Janeck, C.F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58 , 2253. Sugiura, M.; Kobayashi, D. Angew. Chem. Int. Ed. 2005, 44, 5176. Friestad, G. K. Eur. Chem. Rev. 2010, 110, 1386). In recent years, with the rapid development of transition metal catalysis and the continuous increase in the types of reactions it catalyzes, the synthesis and transformation reactions involving N,N-disubstituted hydrazone derivatives have attracted more and more attention from scientists, showing a booming development. trends in (Pair, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Angew. Chem. Int. Ed. 2013, 52, 5346. Prieto, A.;...

Claims

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Application Information

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IPC IPC(8): C07C281/14C07C281/12C07D333/22C07D295/215
CPCC07C281/12C07C281/14C07D295/215C07D333/22
Inventor 江焕峰竺传乐伍婉卿陈鹏全
Owner SOUTH CHINA UNIV OF TECH
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