Synthesis method of alpha-oxo-selenoamide derivative

A synthetic method and technology of selenoamide, applied in the direction of organic chemistry, etc., can solve problems such as poor economy, harsh reaction conditions, and high input costs

Active Publication Date: 2021-05-28
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthesis method of alpha-oxo-selenoamide derivative
  • Synthesis method of alpha-oxo-selenoamide derivative
  • Synthesis method of alpha-oxo-selenoamide derivative

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 invention relates to a synthesis method of an alpha-oxo-selenoamide derivative, which comprises the following steps: in a protective atmosphere and an organic solvent, reacting a compound as shown in a formula (I), elemental selenium and 2,2,6,6-tetramethylpiperidine oxide under the action of metal salt at 20-50 DEG C to obtain the alpha-oxo-selenoamide derivative as shown in a formula (II) after the reaction is completed, wherein the metal salt comprises silver salt and / or copper salt. The method disclosed by the invention does not need to use an organic selenium source, is mild in reaction condition, simple and safe to operate and high in atom economy, and has 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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IPC IPC(8): C07D211/14C07D401/06C07D409/06
CPCC07D211/14C07D401/06C07D409/06
Inventor 纪顺俊蔡忠建王典亮
Owner SUZHOU UNIV
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