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Synthetic method of α-oxo-selenoamide derivatives

A synthetic method, the technology of selenoamide, applied in the direction of organic chemistry, etc., can solve the problems of poor economy, harsh reaction conditions, high input cost, etc., and achieve the effect of improving economy and efficiency, high-efficiency synthesis method, and enhancing application value

Active Publication Date: 2022-04-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, some disadvantages of the method for synthesizing selenoamide are as follows: 1) the reaction conditions are harsh, and reaction conditions such as high temperature and high pressure need to be used; 2) most of the selenium sources come from highly toxic selenides; Selenium reagent, poor economy, high input cost

Method used

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  • Synthetic method of α-oxo-selenoamide derivatives
  • Synthetic method of α-oxo-selenoamide derivatives
  • Synthetic method of α-oxo-selenoamide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of 1-phenyl-2-(2,2,6,6-tetramethylpiperidinyl)-2-selenoacetamide (20)

[0040] Weigh 0.9mmol phenylacetylene (compound corresponding to number (1), 0.0919g), 0.9mmol selenium powder (0.0710g), 0.3mmol 2,2,6,6-tetramethylpiperidine oxide (0.0468g), Add 0.9mmol of silver fluoride (0.1141g) to an 8mL reaction flask, add 3mL of N,N-dimethylacetamide as a solvent, stir and react at 50°C for 10 hours; Chromatographic separation (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) is 1:20) , to obtain 0.0787 g of the reaction product.

[0041] The above-mentioned reaction product is characterized, and the result is: 1 H NMR (400MHz, deuterated chloroform) δ8.06-8.03(m,2H),7.96-7.36(m,3H),2.35(s,1H),2.15(s,6H),1.90-1.85(m,3H) ), 1.65(s,3H), 1.51(s,2H), 1.33(s,3H)ppm; according to the characterization data, the rea...

Embodiment 2

[0043] Synthesis of 1-(4-methylphenyl)-2-(2,2,6,6-tetramethylpiperidinyl)-2-selenoacetamide (21)

[0044] Weigh 0.9mmol 4-methylphenylacetylene (compound corresponding to number (2), 0.1045g), 0.9mmol selenium powder (0.0710g), 0.3mmol 2,2,6,6-tetramethylpiperidine oxide (0.0468g), 0.9mmol silver fluoride (0.1141g) in an 8mL reaction flask, add 3mL of N,N-dimethylacetamide as a solvent, stir and react at 50°C for 10 hours; After vacuum concentration and column chromatography separation (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) 1:20), to obtain 0.0505g reaction product.

[0045] The above-mentioned reaction product is characterized, and the result is: 1 H NMR (400MHz, deuterated chloroform) δ = 7.94 (d, J = 8.0Hz, 2H), 7.19 (d, J = 8.0Hz, 2H), 2.38 (s, 3H), 2.15 (s, 6H), 1.89 -1.85(m,3H), 1.65(s,3H), 1.33(s,3H), 1....

Embodiment 3

[0047] Synthesis of 1-(4-bromophenyl)-2-(2,2,6,6-tetramethylpiperidinyl)-2-selenoacetamide (29)

[0048] Weigh 0.9mmol 4-bromophenylacetylene (compound corresponding to numbering (10), 0.1629g), 0.9mmol selenium powder (0.0710g), 0.3mmol 2,2,6,6-tetramethylpiperidine oxide (0.0468g), 0.9mmol silver fluoride (0.1141g) in an 8mL reaction flask, add 3mL of N,N-dimethylacetamide as a solvent, stir and react at 50°C for 10 hours; After vacuum concentration and column chromatography separation (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) was 1:20), and 0.0509 g of the reaction product was obtained.

[0049] The above-mentioned reaction product is characterized, and the result is: 1 H NMR (400MHz, deuterated chloroform) δ = 7.92 (d, J = 12.0Hz, 2H), 7.52 (d, J = 8.0Hz, 2H), 2.37 (s, 1H), 2.12 (s, 6H), 1.91 -1.84 (s, 3H), ...

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Abstract

The present invention relates to a kind of synthetic method of α-oxo-selenoamide derivative, comprising the following steps: in protective atmosphere and organic solvent, the compound shown in formula (I), selenium simple substance and 2,2,6, 6-Tetramethylpiperidinium oxide reacts at 20-50°C under the effect of metal salt, and the α-oxo-selenoamide derivative shown in formula (II) is obtained after the reaction is complete, and the metal salt includes silver salt and / or copper salts. The method of the invention does not need to use an organic selenium source, has mild reaction conditions, simple and safe operation, high atom economy, good functional group tolerance and substrate universality.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing alpha-oxo-selenoamide derivatives. Background technique [0002] Selenamides are widely used in the synthesis of five-membered and six-membered selenium-containing heterocycles, and are important intermediates in organic synthesis. Due to the existence of the carbon-selenium double bond in the selenoamide molecule, its chemical properties are active and can react with many compounds. Therefore, selenoamide can be used to synthesize many biologically active heterocyclic compounds containing selenium and nitrogen, such as selenazole and its derivatives, 2-aryl-4,5-dihydroselenazole quinoline, etc., and can also be used to synthesize other Selenium-containing compounds such as selenoesters, selenides, etc. [0003] At present, some disadvantages of the method for synthesizing selenoamide are as follows: 1) the reaction conditions are harsh, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/14C07D401/06C07D409/06
CPCC07D211/14C07D401/06C07D409/06
Inventor 纪顺俊蔡忠建王典亮
Owner SUZHOU UNIV