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4-cyano-5-(3-indolyl)oxazole compounds and preparation method thereof

A technology of indolyl and oxazoles, which is applied in the field of 4-cyano-5-oxazoles and their preparation, can solve the problems of unfriendly environment, high cost, high reaction temperature, etc., and achieve atom economy and environmental friendliness , simple steps, and easy-to-obtain raw materials

Active Publication Date: 2019-12-03
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the problems of unfriendly environment, high cost (using metal palladium and copper acetate), and high reaction temperature

Method used

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  • 4-cyano-5-(3-indolyl)oxazole compounds and preparation method thereof
  • 4-cyano-5-(3-indolyl)oxazole compounds and preparation method thereof
  • 4-cyano-5-(3-indolyl)oxazole compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 5-(1H-indol-3-yl)-2-phenyloxazole-4-carbonitrile (1a)

[0033]

[0034] 3-(1H-indol-3-yl)-3-oxopropanecyanide (92mg, 0.5mmol), benzylamine (107mg, 1mmol), N,N-dimethylformamide (3 mL), iodine (32mg, 0.125mmol), tert-butanol peroxide (0.28mL, 70% aqueous solution, 2.0mmol) were successively added in a 25mL Schlenk bottle, placed in an oil bath for reaction, the reaction temperature was controlled at 60°C, and the reaction was carried out for 7 hours. After the reaction was over, the organic solvent was removed under reduced pressure; eluting with petroleum ether / ethyl acetate and separated on a silica gel column to obtain 5-(1H-indol-3-yl)-2-phenyloxazole-4-carbonitrile ( 1a) 110 mg, yield 77%. 1 H NMR (400MHz, DMSO-d 6 )δ12.16(s,1H),8.16(d,J=1.8Hz,1H),8.08(ddd,J=9.1,4.1,1.9Hz,3H),7.61–7.53 (m,4H),7.31–7.22 (m,2H). 13 C NMR (101MHz, DMSO-d 6 )δ158.80,157.48,136.64,131.77,129.75,127.98,126.60,125.87,123.90,123.56,121.98,120.41,115.21,113.14...

Embodiment 2

[0035] Example 2: Synthesis of 5-(1H-indol-3-yl)-2-(4-toluene)oxazole-4-carbonitrile (1b)

[0036]

[0037] 3-(1H-indol-3-yl)-3-oxopropylcyanide (92mg, 0.5mmol), 4-methylbenzylamine (121mg, 1mmol), N,N-dimethylformamide (3mL ), iodine (32mg, 0.125mmol), and tert-butanol peroxide (0.28mL, 70% aqueous solution, 2.0mmol) were successively added into a 25mL Schlenk bottle, placed in an oil bath for reaction, and the reaction temperature was controlled at 60°C. After 7 hours, after the reaction was over, the organic solvent was removed under reduced pressure; eluted with petroleum ether / ethyl acetate, separated on a silica gel column to obtain 5-(1H-indol-3-yl)-2-(4-toluene)oxazole -4-carbonitrile (1b) 116 mg, yield 78%. 1 H NMR (300MHz, DMSO-d 6)δ12.23–12.11(m,1H),8.19(d,J=2.9Hz,1H),8.14–8.06 (m,1H),7.99(d,J=8.0Hz,2H),7.64–7.51(m ,1H),7.42(d,J=8.0Hz,2H),7.36–7.22(m,2H),2.40(s,3H). 13 C NMR (75MHz, DMSO-d 6 )δ159.16,157.27,141.99,136.70,130.40,128.00,126.68,123.96,123.61,12...

Embodiment 3

[0038] Example 3: Synthesis of 5-(1H-indol-3-yl)-2-(2-furan)oxazole-4-carbonitrile (1c)

[0039]

[0040] 3-(1H-indol-3-yl)-3-oxopropanecyanide (92mg, 0.5mmol), 2-furylmethylamine (97mg, 1mmol), N,N-dimethylformamide (3mL) , iodine (32mg, 0.125mmol), tert-butanol peroxide (0.28mL, 70% aqueous solution, 2.0mmol) were successively added in a 25mL Schlenk bottle, and placed in an oil bath for reaction. The reaction temperature was controlled at 60°C. Reaction 7 Hours, after the reaction was over, the organic solvent was removed under reduced pressure; eluted with petroleum ether / ethyl acetate, separated on a silica gel column to obtain 5-(1H-indol-3-yl)-2-(2-furan)oxazole- 4-carbonitrile (1c) 82 mg, yield 60%. 1 H NMR (300MHz, DMSO-d 6 )δ12.21(s,1H),8.18(s,1H),8.13–7.92(m,2H),7.69–7.49 (m,1H),7.43(d,J=3.5Hz,1H),7.37–7.20 (m,2H),6.81(dd,J=3.6,1.8Hz,1H). 13 C NMR (75MHz, DMSO-d 6 )δ156.92,151.66,146.95,141.15,136.69,128.15,123.93,123.67,122.04,120.45,115.03,114.11, 113.23,1...

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Abstract

Provided are a 4-cyano-5-(3-indolyl) oxazole compound and a preparation method thereof. 3- (1H-indole-3-group)-3-oxy propionitrile and benzylamine are used as raw materials, and 5-(3-indole) oxazole is a heterocyclic skeleton. The formula is as shown in the description, wherein R1 is hydrogen, methyl, ethyl, tertiary butyl, tertiary butyl oxy carbonyl or benzyl, R2 is halogen, ester, carboxyl, cyano, amino or methoxy; benzylamine Ar is alkyl or alkoxy-substituted aromatic hydrocarbon, halogenated aromatics or heteroaromatic aromatics, iodisan is one of iodine, potassium iodide, sodium iodide,tetrabutyl ammonium iodide, sulfonium iodate salt, cesium iodide and N-Iodosuccinimide, oxidizing agent is one of hydrogen peroxide, peroxy tert butyl alcohol, potassium hydrogen persulfate, ditert butyl peroxide and chloramine salt, and solvent is one or two of ethyl acetate, acetonitrile, N, N-dimethylformamide, diethyl ether, dimethyl sulfoxide, 1,2-dichloroethane, methyl alcohol, ethyl alcohol, isopropanol, n-butyl ether, n-butyl alcohol, benzene, methylbenzene, 1,4-dioxane, methyl tert-butyl ether, dichloromethane, cyclohexane, petroleum ether, carbon tetrachloride, trichloromethane and tetrahydrofuran.

Description

technical field [0001] The invention relates to 4-cyano-5-(3-indolyl)oxazole compounds and a preparation method thereof, belonging to the field of organic synthesis chemistry. Background technique [0002] 5-(3-indolyl)oxazole is an important class of heterocyclic skeleton, which exists in many natural alkaloids, and has been widely used as a dominant skeleton in the field of medicinal chemistry. 5-(3-Indolyl)oxazoles have a wide range of biological activities, such as antiepileptic, monoamine oxidase inhibitor, anticonvulsant, antibacterial, lipid peroxidation inhibitor, and antitumor activity. The cyano group is an important chemical functional group, which can not only be easily converted into amides, carboxylic acids, imidates, amidines and methylamines, but also be introduced into some lead compounds in drug development. The traditional reported synthesis method of 5-(3-indolyl)oxazole has the disadvantages of long time, many steps, harsh conditions and limited substra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/04C07D413/14
CPCC07D413/04C07D413/14
Inventor 刘培均刘小卒
Owner ZUNYI MEDICAL UNIVERSITY
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