Method for the effective synthesis of optically active oxazoline-2-ketone derivative

An optically active, oxazoline technology, used in the field of bioactivity of fungicides and herbicides

Inactive Publication Date: 2009-11-25
HUAZHONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far there is no relevant C catalyzed by o-chlorothiourea (2-CPU) and N,N-lutidine (DMAP). 2 Research on the organocatalytic tandem reaction of symmetrical chiral sulfur ylides and nitroalkenes. The reaction raw materials are simple and e

Method used

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  • Method for the effective synthesis of optically active oxazoline-2-ketone derivative
  • Method for the effective synthesis of optically active oxazoline-2-ketone derivative
  • Method for the effective synthesis of optically active oxazoline-2-ketone derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] preparation of

[0019] At room temperature, in a 50mL round bottom flask, add 29.8mg trans-β-nitrostyrene (1 chemical equivalent (equiv), 0.2mmol), 3.74mg 2-CPU (10mol%, 0.02mmol), 2.44mg DMAP (10mol %, 0.02mmol) and 20mL solvent (V 甲苯 :V 二氯甲烷 = 4:1), stirring and dissolving, after half an hour, the reaction system turned pale yellow, and 107.6mg (1.25equiv, 0.25mmol) chiral sulfur ylide 3a was added to the system, and the reaction was continued until TLC (pure ethyl acetate was developed as Reagent) detection reaction is complete, column chromatography purification (V 石油醚 / V 乙酸乙酯 / V 二氯甲烷 =16:5:4), 38.0 mg of the target compound was obtained, with a yield of 71%.

[0020] Elemental analysis: measured value C% 72.13H% 5.14N% 5.58;

[0021] Calculated C% 71.90H% 4.90N% 5.24.

[0022] 1 H NMR (400MHz, CDCl 3 ) δ (ppm) 7.94 (d, J = 8.0Hz, 2H), 7.61 (t, J = 7.2Hz, 1H), 7.47 (t, J = 6.4Hz, 2H), 7.44-7.34 (m, 5H), 6.30 (s, 1H), 5.46 (d, J=5.2Hz, 1H), 5.32 (d, J=5....

Embodiment 2

[0027] preparation of

[0028] At room temperature, add 35.8 mg trans-β-nitro-4-methoxystyrene (1 equiv), 0.2 mmol), 3.74 mg 2-CPU (10 mol%, 0.02 mmol), 2.44 mg DMAP into a 50 mL round bottom flask (10mol%, 0.02mmol) and 20mL solvent (V 甲苯 :V 二氯甲烷 = 4:1), stirring and dissolving, after half an hour, the reaction system turned pale yellow, and 107.6mg (1.25equiv, 0.25mmol) chiral sulfur ylide 3a was added to the system, and the reaction was continued until TLC (pure ethyl acetate was developed as Reagent) detection reaction is complete, column chromatography purification (V 石油醚 / V 乙酸乙酯 / V 二氯甲烷 =16:5:4), 32.1 mg of the target compound was obtained, with a yield of 54%.

[0029] Elemental analysis: measured value C% 68.83H% 5.30N% 4.59;

[0030] Calculated C% 68.68H% 5.09N% 4.71.

[0031] 1 H NMR (400MHz, CDCl 3 ) δ (ppm) 7.94 (d, J = 7.6Hz, 2H), 7.62 (t, J = 7.6Hz, 2H), 7.47 (t, J = 7.6Hz, 2H), 7.33 (d, J = 8.0Hz, 2H), 6.93(d, J=8.4Hz, 2H), 5.88(s, 1H), 5.45(d, J=5.6...

Embodiment 3

[0036] preparation of

[0037]At room temperature, in a 50mL round bottom flask, add 36.7mg trans-β-nitro-4-chlorostyrene (1equiv, 0.2mmol), 3.74mg 2-CPU (10mol%, 0.02mmol), 2.44mg DMAP (10mol%) , 0.02mmol) and 20mL solvent (V 甲苯 :V 二氯甲烷 = 4:1), stirring and dissolving, after half an hour, the reaction system turned pale yellow, and 107.6mg (1.25equiv, 0.25mmol) chiral sulfur ylide 3a was added to the system, and the reaction was continued until TLC (pure ethyl acetate was developed as Reagent) detection reaction is complete, column chromatography purification (V 石油醚 / V 乙酸乙酯 / V 二氯甲烷 =16:5:4), 41.0 mg of the target compound was obtained, with a yield of 68%.

[0038] Elemental analysis: measured value C% 63.75 H% 3.65 N% 4.48;

[0039] Calculated for C% 63.69 H% 4.01 N% 4.64.

[0040] 1 H NMR (400MHz, CDCl 3 ) δ (ppm) 7.94 (d, J = 7.6Hz, 2H), 7.63 (t, J = 7.2Hz, 1H), 7.48 (t, J = 7.6Hz, 2H), 7.38-7.32 (m, 4H), 6.62 (s, 1H), 5.39 (d, J=5.6Hz, 1H), 5.32 (d, ...

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Abstract

The invention discloses a method for the effective synthesis of optically active oxazoline-2-ketone derivative. The optically active oxazoline-2-ketone derivative has a structure represented by the formula (I), wherein, R is phenyl, para-methoxyphenyl, para-chlorophenyl, para-fluorophenyl, ortho-chlorophenyl, ortho-methoxyphenyl, meta-bromophenyl, 1-naphthyl, para-bromophenyl, para-nitrophenyl, para-methylphenyl or 3,4-difluorophenyl; R is phenyl, para-methylphenyl, para-methoxyphenyl, para-fluorophenyl, para-chlorophenyl, para-bromophenyl or 2-furyl. Such compounds can be obtained by means of high diastereoselectivity and high enantioselectivity of tandem reaction of organically catalytic C2 symmetrical chiral sulfur ylide and nitroolefin.

Description

technical field [0001] The present invention relates to a synthetic method of optically active oxazolin-2-one compounds and their biological activities as fungicides and herbicides. Background technique [0002] Oxazolin-2-ones and their derivatives are a class of heterocyclic compounds with a wide range of biological activities and important intermediates in organic synthesis. In the mid-eighties of the twentieth century, DuPont Company reported for the first time the synthesis of such fungicides (e.g., DuP-721, 1), and confirmed that they have good bactericidal activity, and many of these compounds have also successfully carried out clinical trials. In 2000, the representative compound Linezolid (2) was approved by the Food and Drug Administration and sold in the market under the trade name of Zyvox. As the only class of novel antibacterial agents, oxazolin-2-one compounds have been developed by leaps and bounds. Therefore, no matter for chemists in academia or industry, ...

Claims

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Application Information

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IPC IPC(8): C07D263/24C07D413/06A01N43/76A01P1/00A01P3/00A01P13/00
Inventor 肖文精明志会陆良秋安静
Owner HUAZHONG NORMAL UNIV
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