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A kind of synthetic method of n-nitroso-2-alkaminooxy aldehyde compound

A technology of an alkanoylaminooxy aldehyde and a synthesis method is applied in the field of synthesis of N-nitroso-2-alkanoylaminooxy aldehyde compounds, and can solve the problems of pre-functionalization of raw materials, environmental pollution of metal catalyst waste, and the like, Achieve the effect of green reaction solvent, mild conditions and wide application range

Active Publication Date: 2021-06-04
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method is relatively reliable, there are still problems such as the pre-functionalization of raw materials, the use of metal catalysts, and the serious pollution of waste to the environment.
It should be pointed out that starting from readily available raw materials and using safe and green reagents to directly complete the one-pot efficient construction of N-nitroso-2-alkylaminooxyaldehyde compounds, there is no literature report yet.

Method used

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  • A kind of synthetic method of n-nitroso-2-alkaminooxy aldehyde compound
  • A kind of synthetic method of n-nitroso-2-alkaminooxy aldehyde compound
  • A kind of synthetic method of n-nitroso-2-alkaminooxy aldehyde compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013]

[0014] Add compound 1a (0.2mmol, 32mg), acetone (acetone, 0.5mL) and water (H 2 2,2,6,6-Tetramethyl-1-oxypiperidine tetrafluoroborate (0.4 mmol, 97 mg) and TBN (98 wt%, 0.3 mmol, 36 μL) were added. The reaction was stirred at room temperature under an air atmosphere for 1 hour, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated through a silica gel column (petroleum ether / ethyl acetate=20:1, v / v) to obtain product 2a (49 mg, 68%) as a yellow liquid. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ:1.11-1.13(m,12H),1.32-1.44(m,5H),1.58-1.74(m,5H),4.02-4.12(m,3H),7.35-7.39(m,1H),7.45- 7.53(m,4H),9.79(d,J=3.6Hz,1H). 13 CNMR (100MHz, CDCl 3 )δ: 17.1, 20.3, 20.4, 21.6, 27.4, 33.9, 34.2, 40.0, 40.1, 43.4, 60.0, 60.6, 87.6, 119.6, 127.5, 129.6,...

Embodiment 2

[0016] Add compound 1a (0.2mmol, 32mg) and acetone (1mL) in a 15mL reaction flask, then add 2,2,6,6-tetramethyl-1-piperidine tetrafluoroborate (0.4mmol, 97mg ) and TBN (98wt%, 0.3mmol, 36μL). The reaction was stirred at room temperature under an air atmosphere for 1 hour, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20:1, v / v) to obtain yellow liquid product 2a (27 mg, 37%).

Embodiment 3

[0018] Add compound 1a (0.2mmol, 32mg) and water (1mL) in a 15mL reaction flask, then add 2,2,6,6-tetramethyl-1-piperidine tetrafluoroborate (0.4mmol, 97mg ) and TBN (98wt%, 0.3mmol, 36μL). The reaction was stirred at room temperature under an air atmosphere for 1 hour, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=20:1, v / v) to obtain yellow liquid product 2a (30 mg, 42%).

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Abstract

The invention discloses a method for synthesizing N-nitroso-2-alkylaminooxyaldehyde compounds, belonging to the technical field of organic synthesis. The main points of the technical scheme of the present invention are as follows: the present invention directly synthesizes a compound containing various functional groups through a one-pot multi-component series reaction between N-aryl substituted saturated heterocyclic compounds, tert-butyl nitrite and oxyammonium salt. N-Nitroso-2-Alkylaminooxyaldehyde compounds, this reaction not only directly constructs N-Nitroso compounds, but also generates alkylaminooxy and aldehyde functional groups at the same time, the whole process is simple and efficient; The synthesis process does not need to use any metal catalyst, the reaction solvent is green, and has the characteristics of economy, greenness and environmental friendliness; the reaction is carried out below 60°C, the conditions are mild, and the operation is simple; the substrate has a wide range of applications. Therefore, the present invention provides an economical, practical and environmentally friendly new method for the synthesis of N-nitroso-2-alkylaminooxyaldehyde compounds.

Description

technical field [0001] The invention discloses a method for synthesizing N-nitroso-2-alkanooxyaldehyde compounds, which belongs to the technical field of organic synthesis. Background technique [0002] N-nitroso compounds are an important class of organic compounds, mainly because N-nitroso itself is an important guiding group and has rich reactivity, which can be easily converted into amino, hydrazine and other different functional groups, and these functional groups can endow the corresponding parent compound with specific functions. On the other hand, alkaminooxyaldehyde compounds are important structural units of many natural products, drugs and functional materials, and have important research value in the fields of biopharmaceuticals, pesticides and industrial dyes. [0003] At present, the synthesis of N-nitroso compounds is generally prepared by the nitrosation reaction of secondary amines and sodium nitrite promoted by Lewis acid. The synthesis of alkaminooxy ald...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/94
CPCC07D211/94
Inventor 何艳范学森张新迎郑智
Owner HENAN NORMAL UNIV