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Spiro indolinone compound, and preparation method and application thereof

The technology of a compound, aurone, is applied in the field of spiro-indolinone compounds and their preparation, which can solve the problems of lack of research results and blanks, and achieve the goals of expanding the application range, convenient post-processing, and good tobacco mosaic virus activity Effect

Active Publication Date: 2019-04-23
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Orange ketone contains active extracyclic double bonds, which can undergo cycloaddition reaction with 1,3-dipole to construct spiro compounds containing benzofuranone, but there is a lack of related research results in the prior art, and benzofuranone The application of spiro compounds of furanone in anti-plant virus is still blank

Method used

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  • Spiro indolinone compound, and preparation method and application thereof
  • Spiro indolinone compound, and preparation method and application thereof
  • Spiro indolinone compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016]

[0017] Weigh 0.0886g N-methylisatin (0.55mmol), 0.0588g sarcosine (0.66mmol) and 0.1191g 6-hydroxyaurone (0.5 mmol) and dissolve them in 4mL of methanol, stir at room temperature for 3h, detect by TLC, confirm The reaction has been completed, the methanol solvent is removed under reduced pressure, and a white solid is obtained by methanol recrystallization, which has the formula The compound of the structure, the yield is 65%. The compound with the structure (I-1) was determined, and its m.p. was 242.7-243.4°C; 1 H NMR (400MHz, DMSO-d 6 )δ:10.86(s,1H),7.37~7.35(m,2H),7.28(dd,J=7.6,1.2Hz,1H),7.26~7.18(m,5H),6.98(td,J=7.5, 1.0Hz, 1H), 6.84(d, J=7.7Hz, 1H), 6.32(dd, J=8.5, 1.9Hz, 1H), 5.99 (d, J=1.8Hz, 1H), 4.15~4.03(m, 2H), 3.45(t, J=7.5Hz, 1H), 3.06(s, 3H), 2.08(s, 3H); 13 C NMR (100MHz, DMSO-d 6 )δ: 196.7, 173.3, 172.6, 167.0, 144.7, 135.1, 130.0 (2C), 129.6, 127.8 (2C), 127.0, 126.5, 125.5, 123.7, 122.0, 112.1, 111.4, 108.1, 97.2, 946.5, 7 , 51.4, 34.2, 25....

Embodiment 2

[0019]

[0020] Accurately weigh 0.1051g N-ethyl isatin (0.60mmol), 0.0633g D-proline (0.55mmol) and 0.1191g 6-hydroxyaurone (0.5mmol) and dissolve in 4mL toluene, stir, reflux for 48h, TLC Detect to confirm that the reaction has been completed, remove the toluene solvent under reduced pressure, and use methanol to recrystallize to a white solid, which has the formula The compound of the structure, the yield is 66%.

[0021] Determination of the compound with structure (I-2), its m.p.212.0~212.6°C; 1 H NMR (400MHz, DMSO-d 6 )δ:10.90(s,1H),7.48(dd,J=7.6,1.2Hz,1H),7.37~7.35(m,2H),7.27~7.22(m,3H),7.19~7.14(m,2H) ,7.00(td,J=7.6,1.1Hz,1H),6.90(d,J=7.8Hz,1H),6.32(dd,J=8.5,1.9Hz,1H),6.11(d,J=1.9Hz, 1H), 4.78~4.73(m, 1H), 3.75~3.66(m, 1H), 3.61(d, J=10.0 Hz, 1H), 3.53~3.44(m, 1H), 3.35~3.31(m, 1H) ,2.67(t,J=7.7Hz,1H),2.08~1.96(m,2H), 1.87~1.66(m,2H),0.94(t,J=7.0Hz,3H); 13 C NMR (100MHz, DMSO-d 6 )δ:195.7,173.3,172.6,167.0,142.9,134.5,129.9(2C),129.6,128.1,128.0(2C),127.1,125...

Embodiment 3

[0023]

[0024] Accurately weigh 0.0886g N-methyl isatin (0.55mmol), 0.0633g D-proline (0.55mmol) and 0.1261g 6-hydroxyl-2'-methyl orangerone (0.5mmol) and dissolve in 4mL methanol, Raise the temperature to 50°C for 5 hours, TLC detection, confirm the completion of the reaction, remove the methanol solvent under reduced pressure, use methanol and ethyl acetate to recrystallize to obtain a white solid, which has the formula The compound of the structure, the yield is 65%.

[0025] Determination of the compound with structure (I-3), m.p.315.1~315.4°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 10.92(s, 1H), 7.83(d, J=7.6Hz, 1H), 7.50(d, J=7.4Hz, 1H), 7.27(td, J=7.7, 0.8Hz, 1H), 7.22~ 7.18(m, 2H), 7.06~6.99(m, 3H), 6.88(d, J=7.8Hz, 1H), 6.32(dd, J=8.5, 1.9 Hz, 1H), 6.05(d, J=1.8Hz ,1H),4.83~4.78(m,1H),3.99(d,J=9.9Hz,1H),3.54~3.48(m,1H), 3.06(s,3H),2.70(t,J=7.8Hz, 1H), 2.11(s, 3H), 2.07~1.95(m, 2H), 1.82~1.61(m, 2H);13 C NMR (100MHz, DMSO-d 6 )δ: 196.9, 173.8, 172.6, 167.1, 144.3, 136...

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Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a spiro indolinone compound, and a preparation method and application thereof. According to the preparation method, a dispiro[benzofuranone-2,3'- pyrrolidone-2',3''-indolinone] compound is obtained by dissolving an N-substituted indigo derivative, alpha-amino acid and an aurone derivative in an organic solventaccording to a certain proportion in a one-pot synthesizing mode, removing the organic solvent after a TLC detection reaction is ended and recrystallizing; and the preparation method is simple. The dispiro[benzofuranone-2,3'- pyrrolidone-2',3''-indolinone] compound disclosed by the invention shows good activity to plant virus, and particularly has a very good prevention and treatment effect on preventing and treating tobacco mosaic virus.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a spirocyclic indolinone compound and a preparation method and application thereof. Background technique [0002] Spiro compounds have a wide range of physiological and pharmacological activities, and exist in large quantities in drugs and natural alkaloids. Orange ketone, 2-phenylmethylene-3-(2H)-benzofuranone, is a secondary metabolite in plants, not only participates in the process of plant growth and reproduction, gives plants yellow or orange color, but also benefits plants Defense against pathogens and pests and inhibiting the growth of competitive weeds. Orange ketone contains active extracyclic double bonds, which can undergo cycloaddition reaction with 1,3-dipole to construct spiro compounds containing benzofuranone, but there is a lack of related research results in the prior art, and benzofuranone The application of the spiro compound of furanone in an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/20C07D491/22C07D513/22A01P1/00
CPCC07D491/20C07D491/22C07D513/22
Inventor 张敏杨文博钱敏丁建芬仰榴青
Owner JIANGSU UNIV
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