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Alpha-amide carbonyl class compound, derivative and synthesis method thereof

A technology of amine compounds and carbonyl amides, which is applied in the field of α-carbonyl amides, can solve the problems of unavailable raw materials and achieve the effects of easy raw materials, high yield and simple conditions

Inactive Publication Date: 2014-04-02
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its synthesis method has always been a research direction that people are more interested in. There have been a large number of literatures reporting the synthesis methods of various α-carbonyl amides, such as: one of the existing methods is to generate such Compounds (Cvetovich, Raymond J.; DiMichele, Lisa. Organic Process Research & Development, 2006, 944-946.); The second existing method uses rearrangement reactions to generate such compounds (Koikov, L.N.; Terent'ev, P.B.; Yufit, D.S.; Struchkov, Yu.T.; Zubarev, V.E.Mosk.Zhurnal Organiccheskoi Khimii, 1985, 1820-31.); Another existing method is to oxidize the hydroxyl group at the α position to obtain the compound (Haddadin, Makhluf J. ; Tannus, Hana T.Heterocycles, 1984,773-8.); All there is this important defect that raw material is not easy to get in above method, often will just can obtain required raw material through a lot of synthetic steps
[0003] So far, there is a lack of a method for the synthesis of α-carbonyl amides with easy access to raw materials, simple production steps, and low cost

Method used

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  • Alpha-amide carbonyl class compound, derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1N-p-methylphenyl-1-phenyl-alpha-carbonylacetamide

[0030] Take a reaction tube, add 5.6mg of copper bromide, 4mg of 2,2,6,6-tetramethylpiperidine nitrogen oxide, 26.75mg of p-methylaniline, 127.6mg of phenylacetylene, 79mg of pyridine, water 45 microliters, 3 milliliters of toluene, and react at 60°C for 18 hours. After the solvent was evaporated to dryness under reduced pressure, 46 mg of the pure product was obtained by separation on a silica gel column with a yield of 77%.

[0031] Take a reaction tube, add 5.6mg of copper bromide, 4mg of 2,2,6,6-tetramethylpiperidine nitrogen oxide, 267.5mg of p-methylaniline, 25.4mg of phenylacetylene, 79mg of pyridine, water 45 microliters, 3 milliliters of toluene, and react at 60°C for 18 hours. After the solvent was evaporated to dryness under reduced pressure, 44 mg of the pure product was obtained by separation on a silica gel column with a yield of 75%.

[0032] Take a reaction tube and add...

Embodiment 2

[0046] The preparation of embodiment 2N-p-methylphenyl-1-p-methylphenyl-α-carbonylacetamide

[0047] Take a reaction tube, add 5.6mg copper bromide, 4mg 2,2,6,6-tetramethylpiperidine nitrogen oxide, 26.75mg p-methylaniline, 145mg p-methylphenylacetylene, 79mg pyridine under oxygen condition , 45 microliters of water, 3 milliliters of toluene, and react at 60° C. for 18 hours. After evaporating the solvent to dryness under reduced pressure, 42.5 mg of the pure product was obtained through silica gel column separation, with a yield of 67%.

[0048] IR (neat): ν=3322.8, 1693.4, 1656.6, 1604.3, 1589.1, 1525.9, 1280.2, 1160.3, 502.3cm -1 ; 1 H NMR (CDCl 3 , 300MHz): δ=8.91(brs, 1H), 8.35(d, J=8.4Hz, 2H), 7.58(d, J=8.4Hz, 2H), 7.31(d, J=8.1Hz, 2H), 7.20 (d, J=8.1Hz, 2H), 2.44(s, 3H), 2.35(s, 3H); 13 C NMR (CDCl3, 75MHz): δ=186.9, 159.0, 145.9, 135.0, 134.1, 131.7, 130.6, 129.7, 129.3, 119.8, 21.9, 21.0ppm; Ms (70ev): m / z (%): 253.2 (13 )[M + ], 119.1(100); HRMS m / z(ESI) calcd...

Embodiment 3

[0049] The preparation of embodiment 3N-p-methylphenyl-1-m-methylphenyl-α-carbonylacetamide

[0050] Take a reaction tube, add 5.6mg of copper bromide, 4mg of 2,2,6,6-tetramethylpiperidine nitrogen oxide, 26.75mg of p-methylaniline, 145mg of m-methylphenylacetylene, and 79mg of pyridine under oxygen condition , 45 microliters of water, 3 milliliters of toluene, and react at 60° C. for 18 hours. After the solvent was evaporated to dryness under reduced pressure, 32 mg of the pure product was obtained by separation on a silica gel column with a yield of 51%.

[0051] IR (neat): ν=3361.8, 1690.4, 1657.9, 1589.0, 1518.1, 1275.5cm -1 ; 1 H NMR (CDCl 3 , 300MHz): δ=8.90(brs, 1H), 8.18-8.21(m, 2H), 7.60-7.57(m, 2H), 7.47-7.36(m, 2H), 7.19(d, J=8.1Hz, 2H ), 2.43(s, 3H), 2.35(s, 3H); 13 C NMR (CDCl3, 75MHz): δ=187.7, 158.9, 138.3, 135.4, 135.0, 134.1, 133.1, 131.8, 129.7, 128.7, 128.4, 119.9, 21.3, 20.9ppm; Ms(70ev): m / z(%) : 253.2(32)[M + ], 119.1(100); HRMS m / z(ESI) calcd for ...

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Abstract

The invention discloses an alpha-amide carbonyl compound, a derivative and a synthesis method thereof. The synthesis method of the alpha-amide carbonyl compound comprises the following steps of: taking copper as a catalyst under the action of an oxidant and mixing an aryl acetylene class compound, an amine class compound, an organic solvent and an auxiliary together for carrying out an oxidation coupling reaction so as to obtain the alpha-amide carbonyl compound. The invention takes the copper as the catalyst for the first time, oxygen gas as the oxidant and alkyne and amine as raw materials directly to synthesize the alpha-amide carbonyl compound. The method has advantages of high yield, simple condition, easy acquirement of the raw materials, simple reaction equipment, easy industrialized production and the like.

Description

technical field [0001] The invention relates to an amide compound and a synthesis method thereof, in particular to an α-carbonyl amide compound or a derivative thereof and a synthesis method thereof, belonging to the field of α-carbonyl amide compounds. Background technique [0002] α-Carbonyl amides are a class of biologically active, widely present in drugs and important molecular fragments in organisms. Its synthesis method has always been a research direction that people are more interested in. There have been a large number of literatures reporting the synthesis methods of various α-carbonyl amides, such as: one of the existing methods is to generate such Compounds (Cvetovich, Raymond J.; DiMichele, Lisa. Organic Process Research & Development, 2006, 944-946.); The second existing method uses rearrangement reactions to generate such compounds (Koikov, L.N.; Terent'ev, P.B.; Yufit, D.S.; Struchkov, Yu.T.; Zubarev, V.E.Mosk.Zhurnal Organiccheskoi Khimii, 1985, 1820-31.);...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/29C07C231/10
Inventor 焦宁张淳
Owner PEKING UNIV