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Synthetic method of 1-aryl-2-(3-methyl-1-indolyl)-1,2-pyrithyldione derivative

A synthetic method, the technology of methyl indole, applied in the direction of organic chemistry, etc., can solve the problem of no one reporting the synthetic method, and achieve the effect of low cost, mild reaction conditions and good selectivity

Active Publication Date: 2014-12-24
UNIV OF SCI & TECH LIAONING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, no one has reported this type of compound and its synthetic method.

Method used

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  • Synthetic method of 1-aryl-2-(3-methyl-1-indolyl)-1,2-pyrithyldione derivative
  • Synthetic method of 1-aryl-2-(3-methyl-1-indolyl)-1,2-pyrithyldione derivative
  • Synthetic method of 1-aryl-2-(3-methyl-1-indolyl)-1,2-pyrithyldione derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-18

[0025] Example 1-18: Synthesis of 1-(4-bromophenyl)-2-(3-methyl-1-indolyl)-1,2-ethanedione

[0026] Add 3-methylindole 0.5mmol, 65.6mg, 4-bromophenacylglyoxal hydrate 0.5mmol, 115.5mg, copper accelerator and organic solvent into a 25mL two-necked bottle equipped with a magnetic stirrer, and heat to the target Temperature reaction, follow the reaction by high performance liquid chromatography and thin layer chromatography, after 10-16 hours of acylation reaction, after the raw materials are consumed, the reaction solution is cooled to room temperature, ethyl acetate and water are added thereto, and the aqueous phase is purified with ethyl acetate Ester extraction. Collect the organic layer, wash with saturated brine, dry over anhydrous sodium sulfate, filter, collect the filtrate, add silica gel, rotary evaporate, the crude product is separated and purified by silica gel column chromatography, the eluent is petroleum ether, and the target product is obtained, and vacuum dried ...

Embodiment 19-26

[0032] 3-Methylindole 0.5mmol, R 1 (R 2 0.5mmol of )-substituted phenylglyoxal hydrate, 99.9mg of copper acetate monohydrate, 4.0mL of dioxane, and 0.5mL of glacial acetic acid were added to a 25mL two-necked bottle equipped with a magnetic stirrer, and the reaction temperature was 120°C. The acylation reaction took 10-16 hours. Other operating methods and steps are the same as in Example 1, and the specific contents are as shown in Table 2 below:

[0033] Table 2

[0034] Example R 1 R 2 Yield / % 19 Cl H 78 20 F H 73 21 I H 73 22 NO 2 H 68 23 H H 73 24 CH 3 H 67 25 H CH 3 65 26 CH 3 CH 3 69

Embodiment 1

[0035] The structural characterization data of the product obtained in Example 1 is:

[0036] Light yellow solid, m.p.: 152.1-153.2℃. 1 H NMR (500MHz, DMSO-d6 ): δ8.39(s, 1H), 7.96(d, J=8.5Hz, 2H), 7.87(d, J=8.5Hz, 2H), 7.65(d, J=7.0Hz, 1H), 7.46-7.42 (m, 2H), 7.36(s, 1H), 2.22(s, 3H); 13 C NMR (125MHz, DMSO-d 6 )δ 187.84, 163.94, 135.18, 133.16, 132.69, 132.33, 131.46, 130.81, 126.13, 125.43, 122.90, 120.85, 120.08, 116.46, 9.62. HRMS (ESI) calcd for C 17 h 12 NO 2 NaBr[M+Na] + 363.9949, found m / z 363.9947.

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Abstract

The invention discloses a synthetic method of 1-aryl-2-(3-methyl-1-indolyl)-1,2-pyrithyldione derivative. A copper accelerant is adopted to directly synthesize a target product. The method comprises the following steps: taking 3-methyl indole (II) and R1(R2)-substituted phenylglyoxal formaldehyde hydrate (III) as raw materials, adopting the copper accelerant, carrying out acylation reaction at 60-140 DEG C for 10-16 hours to obtain 1-aryl-2-(3-methyl-1-indolyl)-1,2-pyrithyldione (I) derivative reaction liquor, wherein a reaction formula is as shown in the specification. According to the synthetic method disclosed by the invention, relatively cheap and stable copper accelerant is adopted, the R1(R2)-substituted phenylglyoxal formaldehyde hydrate is taken as an acylation reagent to directly carry out acylation reaction with the 3-methyl indole, so that other oxidant or additive is not needed to be added into the system, and thus, the reaction conditions are relatively gentle, the selectivity is good, the yield is high and the cost is low.

Description

technical field [0001] The invention relates to a synthesis method of indole compounds, in particular to a synthesis method of 1-aryl-2-(3-methyl-1-indolyl)-1,2-ethanedione derivatives. Background technique [0002] Indole compounds are an important class of alkaloids, which have significant physiological activities and are widely found in various natural products and medicines (R.J. Sundberg, The Chemistry of Indoles. Academic Press: New York, 1970). In addition, 1,2-dicarbonyl compounds are not only used in photosensitizers (Matsuschita Electric Industrial Co. Ltd. JP Pat., 56098203, 1981), corrosion inhibitors (B.I.Ita et al., Mater.Chem.Phys., 2001, 70 , 330) and photoinitiators (B.Husár et al.J.Phys.Chem.B, 2006, 110, 5315) have important applications, and also widely exist in natural products and medicines (K.C.Nicolaou et al. J.Am.Chem.Soc., 2004, 126, 613; R.M.Wadkins et al.J.Med.Chem., 2005, 48, 2906; B.M.Young et al.J.Med.Chem., 2010, 53, 8709 ; W.Mahabusarakam e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 张志强王翠苹阎京波王绍艳卢公昊迟海军董岩马赛勇付莹李旭李洋刘奎
Owner UNIV OF SCI & TECH LIAONING