Preparation method of cis-N-styryl amide derivative

A technology of styrylamide and phenylethynylamide, applied in the field of preparation of cis-N-styrylamide derivatives, achieving high yield, green post-treatment, and wide substrate range

Active Publication Date: 2021-08-03
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing methods can only synthesize thermodynamically stable trans-N-styrylamides, so developing an efficient and green method to synthesize cis-N-styrylamides has become a new challenge in the field of organic chemistry

Method used

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  • Preparation method of cis-N-styryl amide derivative
  • Preparation method of cis-N-styryl amide derivative
  • Preparation method of cis-N-styryl amide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of (Z)-N-Styryl-N-(p-tolyl)methanesulfonyl

[0025]

[0026] Add 0.1mmol of N-(phenylethynyl)-N-(p-tolyl)methanesulfonamide, 0.2mmol of p-toluenesulfonyl hydrazide, 0.15mmol of sodium carbonate and 1mL of tert-butanol into a 15mL reaction tube, and place In an oil bath at 80°C, react for 12 hours; cool to room temperature, dilute the reaction solution with ethyl acetate, wash three times with water, and wash the organic phase successively with anhydrous Na 2 SO 4 Drying, filtration, concentration and purification by TLC gave 24.1 mg of the target product with a yield of 84%. The NMR and high-resolution mass spectrometry characterizations of the target product obtained in this embodiment are as follows: 1 H NMR (500MHz, Chloroform-d) δ=7.14–7.09(m,4H),7.04–6.97(m,3H),6.91–6.86(m,2H),6.59(d,J=9.0Hz,1H), 6.04(d, J=9.0Hz, 1H), 2.83(s, 3H), 2.14(s, 3H); 13 C NMR (126MHz, Chloroform-d) δ = 137.1, 136.4, 133.8, 129.4, 128.9, 127.6, 127.1, 126.7, 126.3, 121.7...

Embodiment 2

[0028] Preparation of (Z)-4-methyl-N-styryl-N-(p-tolyl)benzenesulfonamide

[0029]

[0030] Add 0.1 mmol of N-(phenylethynyl)-N-(p-tolyl)-p-toluenesulfonamide, 0.2 mmol of p-toluenesulfonyl hydrazide, 0.15 mmol of sodium carbonate and 1 mL of tert-butanol into a 15 mL reaction tube, Placed in an oil bath at 80°C, reacted for 12 hours; cooled to room temperature, diluted the reaction solution with ethyl acetate, washed three times with water, and washed the organic phase successively with anhydrous Na 2 SO 4 Drying, filtration, concentration and purification by TLC gave 25.2 mg of the target product with a yield of 67%. The NMR and high-resolution mass spectrometry characterizations of the target product obtained in this embodiment are as follows: 1 H NMR (500MHz, Chloroform-d) δ=7.48–7.44(m,2H),7.22(td,J=5.9,2.8,4H),7.09–7.02(m,3H),6.91–6.84(m,4H) ,6.53(d,J=9.1,1H),6.03(d,J=9.0,1H),2.40(s,3H),2.18(s,3H); 13 C NMR (126MHz, Chloroform-d) δ = 143.9, 136.9 (d, J = 9.1), 134...

Embodiment 3

[0032] Preparation of (Z)-N-Benzyl-N-Styryl Methanesulfonamide

[0033]

[0034] Add 0.1mmol of N-benzyl-N-(phenylethynyl)methanesulfonamide, 0.2mmol of p-toluenesulfonyl hydrazide, 0.15mmol of sodium carbonate and 1mL of tert-butanol into a 15mL reaction tube, and place at 80°C in an oil bath, reacted for 12h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was successively washed with anhydrous Na 2 SO 4 Drying, filtration, concentration and purification by TLC gave 19.4 mg of the target product with a yield of 65%. The NMR and high-resolution mass spectrometry characterizations of the target product obtained in this embodiment are as follows: 1 H NMR (500MHz, Chloroform-d) δ=7.44–7.41(m,2H),7.39–7.30(m,3H),7.27–7.24(m,3H),7.18(dd,J=7.3,2.2,2H) ,6.20(d,J=8.7,1H),6.14(d,J=8.7,1H),4.53(s,2H),2.81(s,3H); 13 C NMR (126MHz, Chloroform-d) δ = 135.7, 134.4, 128.9 (d, J = 2.8), 128.7, 128.4...

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Abstract

The invention discloses a preparation method of a cis-N-styryl amide derivative, which comprises the following steps of: (1) mixing an N-phenylethynyl amide derivative, p-methylbenzenesulfonyl hydrazide, alkali and an organic solvent, and reacting at 80-90 DEG C for 12-24 hours; (2) diluting the material obtained in the step (1) with ethyl acetate, washing with water, and separating to obtain an organic phase; and (3) carrying out drying, filtering, concentration and column chromatography or thin-layer chromatography on the organic phase obtained in the step (2) to obtain the cis-N-styryl amide derivative. The prepared cis-N-styryl amide derivative has good chemical selectivity, and when a carbon-carbon triple bond participates in the reaction, a cis-configuration product is preferentially generated in the reduction process.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of cis-N-styrylamide derivatives. Background technique [0002] Styrylamines and their derivatives are important motifs in bioactive molecules, agrochemicals, natural products, pharmaceuticals, polymers and functional materials. Furthermore, they act as important precursors of meaningful impurities and transform into various compounds. With the vigorous development of green chemistry, the pursuit of cost-effective, efficient, sustainable and environmentally friendly methods for the selective conversion of alkynes to specific alkenes has attracted increasing attention. However, existing methods can only synthesize thermodynamically stable trans-N-styrylamides, so developing an efficient and green method to synthesize cis-N-styrylamides has become a new challenge in the field of organic chemistry. Contents of the invention [0003] The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/08C07C303/40C07C311/21C07C311/03C07C311/07C07D263/22
CPCC07C303/40C07D263/22C07B2200/09C07C2601/02C07C311/08C07C311/21C07C311/03C07C311/07
Inventor 程国林赵泽民
Owner HUAQIAO UNIVERSITY
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