A kind of synthetic method of 1,3-dimethyl-3-hydroxymethylindolin-2-one compound

A technology for hydroxymethyl indoline and ketone compounds, which is applied in one field to achieve the effects of mild reaction conditions, excellent application value and wide selectivity

Active Publication Date: 2021-11-09
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But so far, there is no literature report on the method of directly synthesizing hydroxymethylindolin-2-one compound with cheap and easy-to-obtain N-methyl-N-aryl-acrylamide

Method used

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  • A kind of synthetic method of 1,3-dimethyl-3-hydroxymethylindolin-2-one compound
  • A kind of synthetic method of 1,3-dimethyl-3-hydroxymethylindolin-2-one compound
  • A kind of synthetic method of 1,3-dimethyl-3-hydroxymethylindolin-2-one compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1～4

[0039] The following examples 1 to 4 are all reacted according to the following reaction equations, mainly to investigate the yield situation of different substrates reacting under optimal conditions:

[0040]

[0041] The specific operation steps are as follows: in a 10 mL round-bottomed flask, N-methyl-N-arylacrylamide (0.6 mmol), potassium monopersulfate (0.9 mmol) and acetonitrile (3 mL) were added in sequence. The obtained mixed solution was stirred and reacted at 90° C., and the reaction progress was tracked by thin layer chromatography, and the reaction time was 24 hours. After the reaction, the extract was concentrated in a rotary evaporator, and purified by column chromatography on silica gel using petroleum ether / ethyl acetate as the eluent.

Embodiment 1

[0043] Compound 1, 78% yield, 1,3-dimethyl-3-hydroxymethylindolin-2-one;

[0044] 3-(hydroxymethyl)-1,3-dimethylindolin-2-one;

[0045]

[0046] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.30(t,J=7.7Hz,1H),7.22(d,J=7.3Hz,1H),7.09(t,J=7.5Hz,1H),6.87(d,J=7.8Hz, 1H), 3.85(d, J=10.8Hz, 1H), 3.74(d, J=10.8Hz, 1H), 3.22(s, 3H), 2.38(s, 1H), 1.40(s, 3H);

[0047] 13 C NMR (100MHz, CDCl 3 ,ppm)δ180.0,143.6,131.8,128.3,122.7,122.7,108.3,67.6,49.9,26.2,19.0;

[0048] HRMS(ESI)m / z Calcd for C 11 H 13 NO 2 + [M + ]: 191.0946; found: 191.0948.

Embodiment 2

[0050] Compound 2, 82% yield, 3-(hydroxymethyl)-1,3,5-trimethylindolin-2-one;

[0051]

[0052] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.10(d,J=7.8Hz,1H),7.03(s,1H),6.77(d,J=8.0Hz,1H),3.84(d,J=10.8Hz,1H),3.72( d, J=10.8Hz, 1H), 3.21(s, 3H), 2.35(s, 3H), 1.40(s, 3H);

[0053] 13 C NMR (100MHz, CDCl 3 ,ppm)δ179.9,141.2,132.4,131.7,128.6,123.6,108.1,67.7,49.9,26.2,21.1,19.0;

[0054] HRMS(ESI)m / z Calcd for C 12 H 15 NO 2 + [M + ]: 205.1103; found: 205.1107.

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Abstract

The invention discloses a method for synthesizing a 1,3-dimethyl-3-hydroxymethylindolin-2-one compound. The method is that N-methyl-N-aryl-acrylamide and potassium hydrogen monopersulfate are carried out in acetonitrile medium to carry out epoxidation-intramolecular Friedel-Crafts alkylation series reaction to generate 1,3-dimethyl-3 -Hydroxymethylindoline-2-one compound; the method has the advantages of mild conditions, simple operation, green environmental protection, easy availability of raw materials, excellent compatibility of substrate functional groups, and high reaction yield.

Description

technical field [0001] The invention relates to a method for synthesizing a 1,3-dimethyl-3-hydroxymethylindolin-2-one compound, in particular to a method for synthesizing potassium monopersulfate under the condition of no metal and no external protonic acid. Promoted N-methyl-N-aryl-acrylamide epoxidation-intramolecular Friedel-Crafts alkylation tandem reaction to synthesize 1,3-dimethyl-3-hydroxymethylindolin-2-one compounds The method belongs to the technical field of organic intermediate synthesis. Background technique [0002] Indolin-2-one is the core structural skeleton of various natural products, widely exists in a variety of biologically active natural products and synthetic drug molecules, and has a wide range of biological and pharmacological activities. The hydroxymethyl functional group can effectively improve the metabolic stability and bioavailability of biologically active molecules, and the development of new synthetic methods for heterocyclic compounds con...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34
CPCC07D209/34
Inventor 何卫民张明中王毅基艳吴建平
Owner HUNAN UNIV OF SCI & ENG
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