Substituted azole penta-heterocyclic derivatives and solvothermal one-pot synthesis method and application thereof

A technology of five-membered heterocycles and derivatives, applied in the field of organic synthesis

Active Publication Date: 2016-06-08
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the solvothermal method is widely used in the synthesis of inorganic materials, but there are few reports on the application in organic synthesis. Experiments have proved that the solvothermal one-pot synthesis method has the advantages of high yield, short time, simple operation, energy saving and environmental protection. , is expected to become a new method for efficiently preparing substituted azole five-membered heterocyclic derivatives, and the application prospect will be very broad

Method used

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  • Substituted azole penta-heterocyclic derivatives and solvothermal one-pot synthesis method and application thereof
  • Substituted azole penta-heterocyclic derivatives and solvothermal one-pot synthesis method and application thereof
  • Substituted azole penta-heterocyclic derivatives and solvothermal one-pot synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The synthesis of embodiment 1,2,5 diphenyloxazole ((II) 1)

[0063]

[0064] Add 25mL of pyridine, 2.39g of N-(2-oxo-2-phenyl)ethylbenzamide and 1.7g of phosphorus pentoxide into a 100mL reaction kettle, mix well, tighten the sealing cap, and put it into an electric blast drying oven , heated from room temperature to a reaction temperature of 120°C, and after constant temperature reaction for 6 hours, stop heating, and naturally cool to room temperature, the mixture was washed with distilled water, dried, recrystallized from ethanol, and weighed to obtain 1.82 g of a light yellow solid (II) 1 , the yield was 82.3%.mp:180.1~183.6℃.IRν(cm -1 ):3045,1584,1483,1443,1126,1062,1020,944,908,820,760,683; 1 H-NMR (CDCl 3 ,400MHz):8.12(dd,J=7.7,1.5Hz,2H),7.74(dd,J=8.2,1.3Hz,2H),7.51–7.44(m,6H),7.35(t,J=7.5Hz, 1H); 13 C-NMR (125MHz, CDCl 3 ):161.5, 151.7, 130.8, 129.4, 129.3, 128.9, 128.4, 127.9, 126.7, 124.6, 123.9; HRMS (MALDI-FTMS) calcdforC 15 h 12 NO + [M+H] + 222...

Embodiment 2

[0065] The synthesis of embodiment 2,2-indolyl-5-phenyloxazole ((II) 2)

[0066]

[0067] Add 25mL of toluene, 2.78g of N-(2-oxo-2-phenyl)ethyl-1H-indole-3-carboxamide and 1.7g of phosphorus pentoxide into a 100mL reaction kettle, mix well, tighten the sealing cap, put Put it into an electric blast drying oven, heat up from room temperature to a reaction temperature of 150°C, and after constant temperature reaction for 6 hours, stop heating and cool down to room temperature naturally, wash the mixture with distilled water, dry, recrystallize with ethanol, weigh, and obtain pale white Solid 2.31g (Ⅱ) 2, the yield is 88.7%.IRν(cm -1 ):3413,3154,2919,1625,1602,1443,1361,1249,1120,914,767,726; 1 H-NMR (400MHz, DMSO-d 6 ):8.10–8.07(m,2H),7.98–7.95(m,2H),7.60–7.48(m,5H),7.25–7.17(m,2H); 13 C-NMR (125MHz, DMSO-d 6 ):158.0, 148.3, 136.4, 130.1, 129.2, 127.2, 125.5, 123.9, 123.5, 122.3, 120.8, 120.3, 119.6, 112.2, 103.6; HRMS (MALDI-FTMS) calcdforC 17 h 13 N2O + [M+H] + 261....

Embodiment 3

[0068] The synthesis of embodiment 3,2-indolyl-5 pyridyl oxazole ((II) 3)

[0069]

[0070] Add 25mL of xylene, 2.78g of N-(2-oxo-2-pyridyl)ethyl-1H-indole-3-carboxamide and 1.7g of phosphorus pentoxide into a 100mL reactor, mix well, and tighten the sealing cap. Put it into an electric blast drying box, heat up from room temperature to a reaction temperature of 150°C, and after constant temperature reaction for 6 hours, stop heating and cool down to room temperature naturally, wash the mixture with distilled water, dry, recrystallize with ethanol, weigh, and obtain a yellow color Solid 2.35g (Ⅱ) 3, the yield is 90%.IRν(cm -1 ):3173,2919,1755,1628,1431,1331,1255,1120,1008,920,803,750,703,614; 1 H-NMR (400MHz, DMSO-d 6 ):9.27(s,1H),8.69(d,J=5.0Hz,1H),8.41(d,J=6.7Hz,1H),8.01(d,J=2.4Hz,1H),7.97(d,J =7.9Hz,1H),7.67(s,1H),7.59(dd,J=7.9,5.0Hz,1H),7.49(d,J=7.9Hz,1H),7.25–7.17(m,2H); 13 C-NMR (100MHz, DMSO-d 6 ):155.9, 150.6, 149.0, 136.4, 132.8, 124.2, 124.1, 123.5, 123.4, 12...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly discloses a series of substituted azole penta-heterocyclic derivatives and a solvothermal one-pot synthesis method thereof. By the adoption of the solvothermal one-pot synthesis method for preparing the target product, reaction time is short, a solvent is not prone to volatilization in an airtight system, recycling can be realized, production cost is effectively reduced, the advantages of energy conservation and environment friendliness are achieved, operation is easy, yield is high, and the prepared substituted azole penta-heterocyclic derivatives have good anti-microbial biological activity and excellent photophysical properties such as electron conductivity, the fluorescence property and the ultraviolet property, thereby having very high development and application value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a substituted azole five-membered heterocyclic derivative and a solvothermal one-pot synthesis method thereof, and also relates to the application of the compound. Background technique [0002] Azole compounds are an important class of nitrogen-containing five-membered heterocyclic compounds. Because they are easy to form hydrogen bonds, coordination bonds, etc., they can play a variety of non-covalent interactions, and have antibacterial, antiviral, Widely used in anti-inflammatory and other applications, it is often used as a pharmacophore in the design of new drugs, and is widely used in the fields of medicine, pesticides and other fields; in terms of photoelectric properties, some azole compounds have excellent electronic properties in electroluminescent devices Transport properties, can be used as photosensitive polymer materials in electroluminescent instruments, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32C07D413/04C07D413/14C07D263/57C07D263/34C07D277/22C07D417/04C07D277/60C07D285/12C07D277/56C07D233/64C07D249/08A61P31/04C09K11/06
CPCC07D233/64C07D249/08C07D263/32C07D263/34C07D263/57C07D277/22C07D277/56C07D277/60C07D285/12C07D413/04C07D413/14C07D417/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1059C09K2211/1092
Inventor 陈连清万子露牛雄雷
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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