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N-acetonitrile dibenzenesulfonimide derivative as well as preparation method and application thereof

A technology based on bisbenzenesulfonimide and acetonitrile, applied in the field of N-acetonitrile bisbenzenesulfonimide derivatives and its preparation, can solve the problems of insufficient product diversity and single type

Active Publication Date: 2021-07-06
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problem that the methods for synthesizing nitriles using vinyl azide compounds are single and the product diversity is insufficient in the prior art

Method used

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  • N-acetonitrile dibenzenesulfonimide derivative as well as preparation method and application thereof
  • N-acetonitrile dibenzenesulfonimide derivative as well as preparation method and application thereof
  • N-acetonitrile dibenzenesulfonimide derivative as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Compound 1a (0.2 mmol), compound 1b (0.3 mmol, 1.5 eq) was dissolved in 3 mLDCM, followed by adding CuCl (0.04 mmol, 0.2 eq), PHEN (0.4 mmol, 2 eq), and reacted in an environment of 50 ° C for 16 h. The reaction was monitored by TLC, and the reaction was completed and the reaction was completed. The reaction solution was poured into 30 mL of water, extracted with ethyl acetate (3 × 10 mL), combined with an organic phase, dried over anhydrous sodium sulfate, and then removed the organic solvent by evaporation, and then chromatography (elution) Liquid is v 石油醚 : V 乙酸乙酯 = 20: 1), obtained by obtaining compound 1c, yield of 78%.

Embodiment 2

[0056] Compound 1a (0.2 mmol), compound 1b (0.3 mmol, 1.5 eq) was dissolved in 3 mLDMF, followed by reacting CuCl (0.04 mmol, 0.2 eq), PHEN (0.4 mmol, 2 eq), and reacted in an environment of 50 ° C for 16 h. The reaction was monitored by TLC, and the reaction was completed and the reaction was completed. The reaction solution was poured into 30 mL of water, extracted with ethyl acetate (3 × 10 mL), combined with an organic phase, dried over anhydrous sodium sulfate, and then removed the organic solvent by evaporation, and then chromatography (elution) Liquid is v 石油醚 : V 乙酸乙酯 = 20: 1), obtained from compound 1C, and the yield was 21%.

Embodiment 3

[0058] Compound 1a (0.2 mmol), compound 1b (0.3 mmol, 1.5 eq) was dissolved in 3 mLDCM, then Cui (0.04 mmol, 0.2 eq), PHEN (0.4 mmol, 2 eq), and reacted in an environment of 50 ° C for 16 h. The reaction was monitored by TLC, and the reaction was completed and the reaction was completed. The reaction solution was poured into 30 mL of water, extracted with ethyl acetate (3 × 10 mL), combined with an organic phase, dried over anhydrous sodium sulfate, and then removed the organic solvent by evaporation, and then chromatography (elution) Liquid is v 石油醚 : V 乙酸乙酯 = 20: 1), obtained from compound 1c, yield of 33%.

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Abstract

The invention belongs to the technical field of organic synthesis chemistry, and particularly provides an N-acetonitrile dibenzenesulfonimide derivative as well as a preparation method and application thereof. The structure of the N-acetonitrile dibenzenesulfonimide derivative is shown as a formula (1), wherein R or R1 is selected from one of hydrogen, halogen, C1-C6 linear chain or branched chain alkyl, C1-C6 linear chain alkoxy, nitryl, an ester group, trifluoromethyl, trifluoromethoxy, acetyl, a fused ring group and a heterocyclic ring group. The synthesis method comprises the following steps of: taking a hydroxyl alkenyl azide compound and N-fluorobenzenesulfonamide as raw materials, and synthesizing the compound shown in the formula (1) under the combined action of an additive and a catalyst. According to the method, the N-acetonitrile dibenzenesulfonimide derivative can be rapidly and effectively synthesized, the reaction condition is mild, and toxic and side products are avoided.

Description

Technical field [0001] The present disclosure belongs to the field of organic synthetic chemistry, and provides an N-acetonitrile bisphenylsulfonimide derivative and a preparation method thereof. Background technique [0002] The statements here only provide background information related to the present disclosure, and it is not necessarily constituting prior art. [0003] Nitrile compounds are compounds containing cyano group (-CN), widely existing in natural products, but also plays an important role in drugs, functional materials and pesticide synthesis, but also occupies in organic synthetic chemistry. A very important position. Currently, the synthetic nitrile compounds are: 1, Sandmeyer reaction, 1884, Sandmeyer converted a diazonium salt into a cyano group using Cu salts to form a corresponding cyano compound. 2, Rosemmed-von Braun reaction, 1914, Rosemmed reported that the halogen can be converted to a cyano group under CUCN catalysis. 3, C-C coupling cyanomalated reactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/48C07C303/40C07C303/44A61P29/00
CPCC07C311/48C07C303/40C07C303/44A61P29/00
Inventor 唐波黄晓晴曹文华方杨刘振华高雯
Owner SHANDONG NORMAL UNIV
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